1-(4-氟苯基)-2-甲基-2-吗啉基-1-丙酮

反应条件: temp:0.00; pressure:0.00; stir:

反应条件: temp:0.00; pressure:0.00; stir:

反应条件: temp:0.00; pressure:0.00; stir:

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

实验步骤: 1.26 g (5.0 mmol) of 1-(4-fluorophenyl)-2-methyl-2-morpholin-4-yl-propan-1-one and 7.0 ml (25.0 mmol) of trimethylolpropane tris(2-mercaptoacetate) are dissolved in 25 ml of dry dimethylformamide, and 10.0 mmol of sodium hydride are added. The solution is stirred at room temperature for 2 h. Then the solution is poured into water. The crude product is extracted with methylene chloride, washed with water, dried over MgSO4, and concentrated. The residue is purified by column chromatography on silica gel with methylene chloride-methanol (100:1) as an eluent. The structure is confirmed by the 1H-NMR spectrum (CDCl3): δ [ppm] 0.93 (t, 3H), 1.31 (s, 6H), 1.44 (q, 2H), 1.95-2.13 (m, 2H), 2.57 (t, 4H), 3.25-3.32 (m, 6H), 3.70 (t, 4H), 4.10-4.15 (m, 6H), 7.33 (d, 2H), 8.51 (d, 2H). The crude product is extracted with methylene chloride washed with water dried over MgSO4 concentrated The residue is purified by column chromatography on silica gel with methylene chloride-methanol (100:1) as an eluent

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

实验步骤: 3.6 g (14.3 mmol) of 1-(4-fluorophenyl)-2-methyl-2-morpholin-4-yl-propan-1-one and 12 g (71.3 mmol) of 1,1,1-trismercaptomethylethane are dissolved in 70 ml of dry dimethylformamide, and 28.6 mmol of sodium hydride are added. The solution is stirred at room temperature for 2 h. Then the solution is poured into water. The crude product is extracted with methylene chloride, washed with water, dried over MgSO4, and concentrated. The residue is purified by column chromatography on silica gel with methylene chloride as an eluent. The structure is confirmed by the 1H-NMR spectrum (CDCl3): δ [ppm] 1.12 (s, 3H), 1.30 (t, 2H), 1.31 (s, 6H), 2.57 (t, 4H), 2.62-2.72 (m, 4H), 3.14 (s, 2H), 3.69 (t, 4H), 7.33 (d, 2H), 8.49 (d, 2H). The crude product is extracted with methylene chloride washed with water dried over MgSO4 concentrated The residue is purified by column chromatography on silica gel with methylene chloride as an eluent

反应条件: temp:40.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: 22.5 g (0.24 mol) of 1,2-ethanedithiol are dissolved in 70 ml of dry dimethylacetamide, 10.0 g of potassium carbonate are added and the solution is heated to about 40° C. 10.1 g o(0.04 mol) of 1-(4-fluorophenyl)-2-methyl-2-morpholine-4-yl-propane-1-one (prepared as described in example 1b) in 30 ml of dry dimethylacetamide are added dropwise. The suspension is stirred for 5 h, then the solid is filtered off and washed with toluene. From the filtrate the excess 1,2-ethanedithiol and toluene are distilled off. The residue is purified by column chromatography on silica gel with ethyl acetate-hexane (20:80) as eluent. The resulting product has a melting point of 92-93° C. The structure is confirmed by the 1H-NMR-spectrum, measured in CDCl3. The signals (δ in ppm) are 1.31 (s,6H), 1.75 (t, 1H), 2.57 (t,4H), 2.80 (q,2H), 3.21 (t,2H), 3.70 (t,4H), 7.29 (d,2H), 8.51 (d,2H). the solid is filtered off washed with toluene From the filtrate the excess 1,2-ethanedithiol and toluene are distilled off The residue is purified by column chromatography on silica gel with ethyl acetate-hexane (20:80) as eluent

反应条件: temp:40.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: 52.8 g (0.488 mol) of 1,3-propanedithiol are dissolved in 100 ml of dry dimethylacetamide, 22.0 g of potassium carbonate are added and the solution is heated to about 40° C. 20.0 g (0.08 mol) of 1-(4-fluorophenyl)-2-methyl-2-morpholine-4-yl-propan-1-one in 50 ml of dry dimethylacetamide are added dropwise over 14 h. The resulting suspension is stirred for additional 5 h, then the solid is filtered off and washed with toluene. From the filtrate the excess 1,3-propanedithiol and toluene are distilled off. The residue is dissolved in ethyl acetate and the resulting solution is washed with saturated ammonium chloride solution, is dried over MgSO4 and concentrated. The residue is recrystallized from ethanol. The obtained product has a melting point of 67-68° C. The structure is confirmed by the 1H-NMR-spectrum, measured in CDCl3. The signals (δ in ppm) are 1.31 (s, 6H), 1.39 (t, 1H), 2.00 (m,2H), 2.57 (t,4H), 2.70 (q,2H), 3.13 (t,2H), 3.69 (t,4H), 7.28 (d,2H), 8.50 (d, 2H). the solid is filtered off washed with toluene From the filtrate the excess 1,3-propanedithiol and toluene are distilled off The residue is dissolved in ethyl acetate the resulting solution is washed with saturated ammonium chloride solution is dried over MgSO4 concentrated The residue is recrystallized from ethanol

反应条件: temp:130.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: 69.3 g (0.35 mol) of (4-fluorophenyl)-3,3-dimethyl-2-methoxyoxirane and 200 ml of dry morpholine are mixed and heated to reflux temperature (about 130° C.). After 26 h, the unreacted excess morpholine is distilled off. The residue is taken up in toluene and washed with water and saturated sodium chloride solution successively. The toluene solution is dried with MgSO4 and is concentrated. The residue, 88.1 g, crystallizes from ethanol with a melting point of 63-66° C. heated the unreacted excess morpholine is distilled off washed with water and saturated sodium chloride solution successively The toluene solution is dried with MgSO4 is concentrated The residue, 88.1 g, crystallizes from ethanol with a melting point of 63-66° C.

反应条件: temp:160.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: 15.08 g (0.06 mol) of 1-(4-fluorophenyl)-2-methyl-2-morpholinopropan-1-one and 5.23 g (0,06 mol) of morpholine are dissolved in 25 ml of dimethyl sulfoxide, and the solution is heated to 160° C. together with 8.3 g (0.06 mol) of potassium carbonate. After 18 hours of stirring at about 160° C. the suspension is cooled down and is poured onto an ice-water mixture. The crystals are filtered off, are washed with water and are recrystallised from ethanol. Melting point 114°-116° C. is cooled down The crystals are filtered off are washed with water are recrystallised from ethanol

反应条件: temp:160.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: 15.08 g (0.06 mol) of 1-(4-fluorophenyl)-2-methyl-2-morpholinopropan-1-one and 5.23 g (0,06 mol) of morpholine are dissolved in 25 ml of dimethyl sulfoxide, and the solution is heated to 160° C. together with 8.3 g (0.06 mol) of potassium carbonate. After 18 hours of stirring at about 160° C. the suspension is cooled down and is poured onto an ice-water mixture. The crystals are filtered off, are washed with water and are recrystallised from ethanol. Melting point 114°-116° C. is cooled down The crystals are filtered off are washed with water are recrystallised from ethanol

反应条件: temp:130.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: 29.43 g (0.15 mol) of 2-(4-fluorophenyl)-3,3-dimethyl-2-methoxyoxirane and 52.3 g (0.60 mol) of morpholine are brought together, and the mixture is heated to reflux temperature (about 130° C.). After 23 hours the excess morpholine is distilled off. The residue is taken up with toluene, and the mixture is extracted with dilute hydrochloric acid. The hydrochloric acid solution is rendered alkaline and is extracted with toluene. The toluene solution is dried with K2CO3 and is concentrated. The residue, 34.0 g, crystallises out from ethyl acetate with a melting point of 63°-66° C. the mixture is heated After 23 hours the excess morpholine is distilled off the mixture is extracted with dilute hydrochloric acid is extracted with toluene The toluene solution is dried with K2CO3 is concentrated The residue, 34.0 g, crystallises out from ethyl acetate with a melting point of 63°-66° C.

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

实验步骤: 1.26 g (5.0 mmol) of 1-(4-fluorophenyl)-2-methyl-2-morpholin-4-yl-propan-1-one and 7.0 ml (25.0 mmol) of trimethylolpropane tris(2-mercaptoacetate) are dissolved in 25 ml of dry dimethylformamide, and 10.0 mmol of sodium hydride are added. The solution is stirred at room temperature for 2 h. Then the solution is poured into water. The crude product is extracted with methylene chloride, washed with water, dried over MgSO4, and concentrated. The residue is purified by column chromatography on silica gel with methylene chloride-methanol (100:1) as an eluent. The structure is confirmed by the 1H-NMR spectrum (CDCl3): δ [ppm] 0.93 (t, 3H), 1.31 (s, 6H), 1.44 (q, 2H), 1.95-2.13 (m, 2H), 2.57 (t, 4H), 3.25-3.32 (m, 6H), 3.70 (t, 4H), 4.10-4.15 (m, 6H), 7.33 (d, 2H), 8.51 (d, 2H). The crude product is extracted with methylene chloride washed with water dried over MgSO4 concentrated The residue is purified by column chromatography on silica gel with methylene chloride-methanol (100:1) as an eluent