Ethanol → 1-Isopropylpiperidin-4-ol

Participants

Reaction Steps

To a cold (0° C.) solution of 1-isopropylpiperidone (purchased at Chemie Brunschwig AG, 100 g, 1.0 eq.) in ethanol (500 mL) was added sodium borohydride (19.3 g, 0.7 eq.) in small portions. The reaction mixture was allowed to warm up to room temperature and was stirred overnight. After concentration in vacuo, ice water (1 kg), sodium hydroxide aqueous solution (28% in mass, 0.5 L) and dichloromethane (1 L) were added. The mixture was stirred vigorously for 4 h and the aqueous layer was extracted with dichloromethane. Combined organic layers were washed with brine, dried over sodium sulfate, filtered and purified by fractionated vacuum distillation (20 mBar). One fraction (95° C. at 20 mBar) was isolated to yield 61.3 g (60%) of the title product as colorless oil. MS (m/e): 144.5 (MH+, 100%).

Provenance & Evidence