N,N-二甲基色胺

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: A solution of formaldehyde (80 mg of a 30% solution) in methanol (15 ml) was added to a stirred solution of 2-[5-(2-methyltetrazol-5-ylmethyl)-1H-indol-3-yl]ethylamine (0.1 g, 0.4 mmol), NaCNBH3 (60 mg) and glacial acetic acid (0.12 g) in methanol (15 ml). The solution was stirred for 2 h, basified with K2CO3 solution and the MeOH removed under vacuum. The crude product obtained after extraction into ethylacetate and removal of solvent was chromatographed through silica-gel eluting with CH2Cl2 /EtOH/NH3 (40:8:1) to give the desired N,N-dimethyltryptamine (96 mg, 87%). The oxalate salt was prepared: mp 185°-187° C. (MeOH/Et2O); (Found: C, 54.42; H, 5.74; N, 22.53. C15H20N6.C2H2O4 requires C, 54.54; H, 5.92; N, 22.45%); δ (360 MHz, D2O) 2.91 (6H, s, 2 of CH3); 3.21 (2H, t, J=7.4 Hz, CH2); 3.47 (2H, J=7.4 Hz, CH2); 4.30 (3H, s, CH3); 4.34 (2H, s, CH2); 7.17 (1H, dd, J=1.5 and 8.4 Hz, Ar-H); 7.33 (1H, s, Ar-H); 7.48 (1H, d, J=8.4 Hz, Ar-H); 7.59 (1H, s, Ar-H). the MeOH removed under vacuum The crude product obtained after extraction into ethylacetate and removal of solvent was chromatographed through silica-gel eluting with CH2Cl2 /EtOH/NH3 (40:8:1)

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: To 250 mg of 3-(2-bromoethyl)indole in a round-bottomed flask, a 10 M excess of dimethylamine (6 mL of 2M in MeOH) was added and the solution was stirred at r.t. overnight. After adding 5 mL sodium bicarbonate (2%), the reaction mixture was extracted with chloroform (3×5 ml) and back extracted with H2O (1×5 mL). The combined extracts were dried over MgSO4 and evaporation of the solvent gave the product in crystalline form. Yield: 0.21 g, 84%, yellowish crystals. m.p.: 45-47° C.; TLC (EtAc:MeOH:acetic acid, 8:2:0.5 v/v/v): RF=0.33. 1H NMR, δ: 10.43 (s, 1H), 7.42-7.06 (m, 5H), 2.68 (m, 4H), 2.26 (S, 6H). 13C NMR (CDCl3): δ 136.5, 124.3, 123.2, 121.2, 119.7, 117.6, 113.4, 111.1, 61.7, 41.2, 22.4. Anal. calcd for C12H16N2: C, 76.55; H, 8.57; N, 14.88%. Found; C, 76.60; H, 8.70; N, 14.70%. the reaction mixture was extracted with chloroform (3×5 ml) back extracted with H2O (1×5 mL) The combined extracts were dried over MgSO4 and evaporation of the solvent gave the product in crystalline form

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: To 250 mg of 3-(2-bromoethyl)indole in a round-bottomed flask, a 10 M excess of dimethylamine (6 mL of 2M in MeOH) was added and the solution was stirred at r.t. overnight. After adding 5 mL sodium bicarbonate (2%), the reaction mixture was extracted with chloroform (3×5 ml) and back extracted with H2O (1×5 mL). The combined extracts were dried over MgSO4 and evaporation of the solvent gave the product in crystalline form. Yield: 0.21 g, 84%, yellowish crystals. m.p.: 45-47° C.; TLC (EtAc:MeOH:acetic acid, 8:2:0.5 v/v/v): RF=0.33. 1H NMR, δ: 10.43 (s, 1H), 7.42-7.06 (m, 5H), 2.68 (m, 4H), 2.26 (S, 6H). 13C NMR (CDCl3): δ 136.5, 124.3, 123.2, 121.2, 119.7, 117.6, 113.4, 111.1, 61.7, 41.2, 22.4. Anal. calcd for C12H16N2: C, 76.55; H, 8.57; N, 14.88%. Found; C, 76.60; H, 8.70; N, 14.70%. the reaction mixture was extracted with chloroform (3×5 ml) back extracted with H2O (1×5 mL) The combined extracts were dried over MgSO4 and evaporation of the solvent gave the product in crystalline form

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: A solution of 4.7 g. (0.015 mole) of N,N-dimethyl-2-(3-ethyl-5-methyl-4-isoxazolyl)-3-indoleacetamide in 47 ml. of tetrahydrofuran under nitrogen is added dropwise to a suspension of 2.28 g. (0.06 mole) lithium aluminum hydride in 50 ml. tetrahydrofuran, while maintaining the reaction at room temperature. The mixture is stirred for 11/2 hours at room temperature, cooled in ice and quenched with 5 ml. water in 50 ml. tetrahydrofuran. The resulting solids are filtered and the filtrate dried over anhydrous magnesium sulfate, filtered and evaporated and the residue crystallized from ether to give 2-(3-ethyl-5-methyl)-4-isoxazolyl)-3-(dimethylaminoethyl)-indole; m.p. 118° to 120° C. the reaction at room temperature cooled in ice quenched with 5 ml The resulting solids are filtered the filtrate dried over anhydrous magnesium sulfate filtered evaporated the residue crystallized from ether

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: A solution of formaldehyde (80 mg of a 30% solution) in methanol (15 ml) was added to a stirred solution of 2-[5-(2-methyltetrazol-5-ylmethyl)-1H-indol-3-yl]etylamine (0.1 g, 0.4 mmol), NaCNBH3 (60 mg) and glacial acetic acid (0.12g) in methanol (15 ml). The solution was stirred for 2 h, basified with K2CO3 solution and the MeOH removed under vacuum. The crude product obtained after extraction into ethylacetate and removal of solvent was chromatographed through silica-gel eluting with CH2Cl2 /EtOH/NH3 (40:8:1) to give the desired N,N-dimethyltryptamine (96 mg, 87%). The oxalate salt was prepared: mp 185°-187° C. (MeOH/Et2O); (Found: C, 54.42; H, 5.74; N, 22.53. C15H20N6. C2H2O4 requires C, 54.54; H, 5.92; N, 22.45%); δ (360 MHz, D2O) 2.91 (6H, s, 2 of CH3); 3.21 (2H, t, J=7.4 Hz, CH2); 3.47 (2H, t, J=7.4 Hz, CH2); 4.30 (3H, s, CH3); 4.34 (2H, s, CH2); 7.17 (1H, dd, J=1.5 and 8.4 Hz, Ar--H); 7.33 (1H, s, Ar--H); 7.48 (1H, d, J=8.4 Hz, Ar--H); 7.59 (1H, s, Ar--H). the MeOH removed under vacuum The crude product obtained after extraction into ethylacetate and removal of solvent was chromatographed through silica-gel eluting with CH2Cl2 /EtOH/NH3 (40:8:1)

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: A solution of formaldehyde (80 mg of a 30% solution) in methanol (15 ml) was added to a stirred solution of 2-[5-(2-methyltetrazol-5-ylmethyl)-1H-indol-3-yl]ethylamine (0.1 g, 0.4 mmol), NaCNBH3 (60 mg) and glacial acetic acid (0.12 g) in methanol (15 ml). The solution was stirred for 2 h, basified with K2CO3 solution and the MeOH removed under vacuum. The crude product obtained after extraction into ethylacetate and removal of solvent was chromatographed through silica-gel eluting with CH2Cl2 /EtOH/NH3 (40:8:1) to give the desired N,N-dimethyltryptamine (96 mg, 87%). The oxalate salt was prepared: mp 185°-187° C. (MeOH/Et2O); (Found: C, 54.42; H, 5.74; N, 22.53.C15H20N6.C2H2O4 requires C, 54.54; H, 5.92; N, 22.45%); δ (360 MHz, D2O) 2.91 (6H, s, 2 of CH3); 3.21 (2H, t, J=7.4 Hz, CH2); 3.47 (2H, t, J=7.4 Hz, CH2); 4.30 (3H, s, CH3); 4.34 (2H, s, CH2); 7.17 (1H, dd, J=1.5 and 8.4 Hz, Ar--H); 7.33 (1H, s, Ar--H); 7.48 (1H, d, J=8.4 Hz, Ar--H); 7.59 (1H, s, Ar--H). the MeOH removed under vacuum The crude product obtained after extraction into ethylacetate and removal of solvent was chromatographed through silica-gel eluting with CH2Cl2 /EtOH/NH3 (40:8:1)

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: A solution of 4.7 g. (0.015 mole) of N,N-dimethyl-2-(3-ethyl-5-methyl-4-isoxazolyl)-3-indoleacetamide in 47 ml. of tetrahydrofuran under nitrogen is added dropwise to a suspension of 2.28 g. (0.06 mole) lithium aluminum hydride in 50 ml. tetrahydrofuran, while maintaining the reaction at room temperature. The mixture is stirred for 11/2 hours at room temperature, cooled in ice and quenched with 5 ml. water in 50 ml. tetrahydrofuran. The resulting solids are filtered and the filtrate dried over anhydrous magnesium sulfate, filtered and evaporated and the residue crystallized from ether to give 2-(3-ethyl-5-methyl)-4-isoxazolyl)-3-(dimethylaminoethyl)-indole; m.p. 118° to 120° C. the reaction at room temperature cooled in ice quenched with 5 ml The resulting solids are filtered the filtrate dried over anhydrous magnesium sulfate filtered evaporated the residue crystallized from ether

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: A solution of 4.7 g. (0.015 mole) of N,N-dimethyl-2-(3-ethyl-5-methyl-4-isoxazolyl)-3-indoleacetamide in 47 ml. of tetrahydrofuran under nitrogen is added dropwise to a suspension of 2.28 g. (0.06 mole) lithium aluminum hydride in 50 ml. tetrahydrofuran, while maintaining the reaction at room temperature. The mixture is stirred for 11/2 hours at room temperature, cooled in ice and quenched with 5 ml. water in 50 ml. tetrahydrofuran. The resulting solids are filtered and the filtrate dried over anhydrous magnesium sulfate, filtered and evaporated and the residue crystallized from ether to give 2-(3-ethyl-5-methyl)-4-isoxazolyl)-3-(dimethylaminoethyl)-indole; m.p. 118° to 120° C. the reaction at room temperature cooled in ice quenched with 5 ml The resulting solids are filtered the filtrate dried over anhydrous magnesium sulfate filtered evaporated the residue crystallized from ether

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: A solution of formaldehyde (80 mg of a 30% solution) in methanol (15 ml) was added to a stirred solution of 2-[5-(2-methyltetrazol-5-ylmethyl)-1H-indol-3-yl]ethylamine (0.1 g, 0.4 mmol), NaCNBH3 (60 mg) and glacial acetic acid (0.12 g) in methanol (15 ml). The solution was stirred for 2 h, basified with K2CO3 solution and the MeOH removed under vacuum. The crude product obtained after extraction into ethylacetate and removal of solvent was chromatographed through silica-gel eluting with CH2Cl2 /EtOH/NH3 (40:8:1) to give the desired N,N-dimethyltryptamine (96 mg, 87%). The oxalate salt was prepared: mp 185°-187° C. (MeOH/Et2O); (Found: C, 54.42; H, 5.74; N, 22.53. C15H20N6.C2H2O4 requires C, 54.54; H, 5.92; N, 22.45%); δ (360 MHz, D2O) 2.91 (6H, s, 2 of CH3); 3.21 (2H, t, J=7.4 Hz, CH2); 3.47 (2H, J=7.4 Hz, CH2); 4.30 (3H, s, CH3); 4.34 (2H, s, CH2); 7.17 (1H, dd, J=1.5 and 8.4 Hz, Ar-H); 7.33 (1H, s, Ar-H); 7.48 (1H, d, J=8.4 Hz, Ar-H); 7.59 (1H, s, Ar-H). the MeOH removed under vacuum The crude product obtained after extraction into ethylacetate and removal of solvent was chromatographed through silica-gel eluting with CH2Cl2 /EtOH/NH3 (40:8:1)