Water → [(1-{4-[3-(2,2-Dimethylpyrrolidin-1-yl)propoxy]phenyl}-cyclo-hexyl)methyl]amine

Participants

Reaction Conditions

Reaction Steps

To a stirred suspension of LiAlH4 (1.0M in diethyl ether, 0.4 ml, 0.40 mmol) at 0° C. under an atmosphere of nitrogen was added 1-{4-[3-(2,2-dimethylpyrrolidin-1-yl)propoxy]phenyl}cyclohexanecarbonitrile (27 mg, 0.079 mmol) in Et2O (15 mL) over 15 minutes maintaining the temperature at 5 to 10° C. The reaction mixture was allowed to warm up to ambient temperature for 20 minutes then refluxed for 30 minutes until complete. The reaction mixture was cooled to 0° C., water (0.5 mL) was added followed by NaOH (2.0M, 1.5 mL) and water (0.5 mL). Ethyl acetate (5 mL) was added and the mixture filtered through a short pad of celite, eluting with ethyl acetate (2×15 mL) and concentrated in vacuo. The compound was purified by column chromatography on Biotage® silica gel, eluting with dichloromethane:methanol:ammonia, 97:3:0.3 to give the title compound as a clear oil (10 mg, 37%). 1H NMR (400 MHz, CDCl3) δ 7.22 (d, 2H), 6.84 (d, 2H), 4.02 (t, 2H), 2.86-2.76 (m, 2H), 2.66 (s, 2H), 2.58-2.50 (m, 2H), 2.16-2.06 (m, 2H), 2.00-2.90 (m, 2H), 1.84-1.72 (m, 2H), 1.70-1.64 (m, 2H), 1.56-1.46 (m, 4H), 1.40-1.32 (m, 4H), 1.02 (s, 6H). HRMS (ESI+) 345.2901 (M+H)+.

Provenance & Evidence