11-(甲氨基)十一烷-1-醇

反应条件: temp:-5.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: 11-methylamino undecan-1-ol (10.07 g, 50.0 mmol) was dissolved in dichloromethane (30 ml). A solution of sodium hydroxide (2.40 g, 60.0 mmol) in water (30 ml) was added. The mixture was cooled to −5° C. and a solution of acrylic acid chloride (4.75 g, 52.5 mmol) and BHT (10 mg) in dichloromethane (30 ml) was added dropwise. Once the addition had ended the reaction mixture was stirred for 2 h at −5° C. and for a further 16 h at RT. Organic and aqueous phases were separated. The aqueous phase was saturated with NaCl and extracted with dichloromethane (2×50 ml). The combined organic phases were dried over Na2SO4, filtered and concentrated on the rotary evaporator. The crude product was purified by means of column chromatography (SiO2/ethyl acetate). 10.38 g (40.6 mmol; 81% yield) of a yellowish liquid was obtained. Once the addition Organic and aqueous phases were separated extracted with dichloromethane (2×50 ml) The combined organic phases were dried over Na2SO4 filtered concentrated on the rotary evaporator The crude product was purified by means of column chromatography (SiO2/ethyl acetate) 10.38 g (40.6 mmol; 81% yield) of a yellowish liquid was obtained

反应条件: temp:-5.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: 11-methylamino undecan-1-ol (10.07 g, 50.0 mmol) was dissolved in dichloromethane (30 ml). A solution of sodium hydroxide (2.40 g, 60.0 mmol) in water (30 ml) was added. The mixture was cooled to −5° C. and a solution of acrylic acid chloride (4.75 g, 52.5 mmol) and BHT (10 mg) in dichloromethane (30 ml) was added dropwise. Once the addition had ended the reaction mixture was stirred for 2 h at −5° C. and for a further 16 h at RT. Organic and aqueous phases were separated. The aqueous phase was saturated with NaCl and extracted with dichloromethane (2×50 ml). The combined organic phases were dried over Na2SO4, filtered and concentrated on the rotary evaporator. The crude product was purified by means of column chromatography (SiO2/ethyl acetate). 10.38 g (40.6 mmol; 81% yield) of a yellowish liquid was obtained. Once the addition Organic and aqueous phases were separated extracted with dichloromethane (2×50 ml) The combined organic phases were dried over Na2SO4 filtered concentrated on the rotary evaporator The crude product was purified by means of column chromatography (SiO2/ethyl acetate) 10.38 g (40.6 mmol; 81% yield) of a yellowish liquid was obtained

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

实验步骤: A solution of 11-bromoundecanol (25.12 g, 0.10 mol) and methylamine (41% in water, 127 ml, 1.50 mol) in ethanol (50 ml) was heated for 7 h to 70° C. and stirred for a further 16 h at ambient temperature. The solvent was distilled off. After cooling the white solid was dissolved in caustic soda (2N, 200 ml) and diethyl ether (300 ml). The phases were separated and the aqueous phase was extracted with diethyl ether (2×100 ml). The combined organic phases were dried over Na2SO4, filtered and concentrated on the rotary evaporator. The crude product was recrystallized from diethyl ether. 13.23 g (65.7 mmol, 67% yield) of a while solid (melting point: 58° C.) was obtained. The solvent was distilled off After cooling the white solid was dissolved in caustic soda (2N, 200 ml) The phases were separated the aqueous phase was extracted with diethyl ether (2×100 ml) The combined organic phases were dried over Na2SO4 filtered concentrated on the rotary evaporator The crude product was recrystallized from diethyl ether

反应条件: temp:95.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: 11.6 g of the N-methyl-N-(11-hydroxyundecyl)amine obtained according to Section 1, 8 g of potassium carbonate powder, 7.18 g of 4-fluorobenzaldehyde and 2 drops of the conventional and known phase transfer catalyst Aliquat® 336 (fatty quaternary ammonium chloride) in 50 ml of dimethylpropyleneurea were stirred for 72 hours at 95° C. Aliquat 336 is a commercial product and constitutes methyl-trioctylammonium chloride. It is a mixture of C8 - and C10 -chains, C8 being predominant. It is used as a phase transfer catalyst and liquid ion exchanger. The reaction mixture was then diluted with 700 ml of water and extracted with three times 50 ml of a solvent mixture of ether and ethyl acetate in a volume ratio of 1:1. The combined extracts were washed with three times 50 ml of water and then dried with sodium sulfate and, after the sodium sulfate had been separated off, were evaporated down. The resulting residue was freed from unconverted benzaldehyde by drying at 60° C. under reduced pressure from an oil pump, this procedure being monitored by thin layer chromatography. The dry product was purified by boiling with active carbon in acetone 12.45 g of 4-[N-methyl-N-(11-hydroxyundecyl)]-amino]-benzaldehyde were obtained, whose IR spectrum (KBr pellet) had bands at 3,400, 2,900, 2,850, 1,660, 1,580, 1,520, 1,460, 1,440, 1,380, 1,310, 1,240, 1,160, 1,050 and 820 cm-1. extracted with three times 50 ml of a solvent mixture of ether and ethyl acetate in a volume ratio of 1:1 The combined extracts were washed with three times 50 ml of water dried with sodium sulfate after the sodium sulfate had been separated off were evaporated down by drying at 60° C. under reduced pressure from an oil pump The dry product was purified were obtained

反应条件: temp:-5.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: 11-methylamino undecan-1-ol (10.07 g, 50.0 mmol) was dissolved in dichloromethane (30 ml). A solution of sodium hydroxide (2.40 g, 60.0 mmol) in water (30 ml) was added. The mixture was cooled to −5° C. and a solution of acrylic acid chloride (4.75 g, 52.5 mmol) and BHT (10 mg) in dichloromethane (30 ml) was added dropwise. Once the addition had ended the reaction mixture was stirred for 2 h at −5° C. and for a further 16 h at RT. Organic and aqueous phases were separated. The aqueous phase was saturated with NaCl and extracted with dichloromethane (2×50 ml). The combined organic phases were dried over Na2SO4, filtered and concentrated on the rotary evaporator. The crude product was purified by means of column chromatography (SiO2/ethyl acetate). 10.38 g (40.6 mmol; 81% yield) of a yellowish liquid was obtained. Once the addition Organic and aqueous phases were separated extracted with dichloromethane (2×50 ml) The combined organic phases were dried over Na2SO4 filtered concentrated on the rotary evaporator The crude product was purified by means of column chromatography (SiO2/ethyl acetate) 10.38 g (40.6 mmol; 81% yield) of a yellowish liquid was obtained

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

实验步骤: A solution of 11-bromoundecanol (25.12 g, 0.10 mol) and methylamine (41% in water, 127 ml, 1.50 mol) in ethanol (50 ml) was heated for 7 h to 70° C. and stirred for a further 16 h at ambient temperature. The solvent was distilled off. After cooling the white solid was dissolved in caustic soda (2N, 200 ml) and diethyl ether (300 ml). The phases were separated and the aqueous phase was extracted with diethyl ether (2×100 ml). The combined organic phases were dried over Na2SO4, filtered and concentrated on the rotary evaporator. The crude product was recrystallized from diethyl ether. 13.23 g (65.7 mmol, 67% yield) of a while solid (melting point: 58° C.) was obtained. The solvent was distilled off After cooling the white solid was dissolved in caustic soda (2N, 200 ml) The phases were separated the aqueous phase was extracted with diethyl ether (2×100 ml) The combined organic phases were dried over Na2SO4 filtered concentrated on the rotary evaporator The crude product was recrystallized from diethyl ether