2-Methylpyrrolidine → HCID 178426194, compound

Reaction equation

Cl[CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([C@H:12]2[CH2:17][CH2:16][C@H:15]([OH:18])[CH2:14][CH2:13]2)=[CH:8][CH:7]=1.[Na].[CH3:20][CH:21]1[CH2:25][CH2:24][CH2:23][NH:22]1>C(#N)C>[OH:18][C@H:15]1[CH2:16][CH2:17][C@H:12]([C:9]2[CH:10]=[CH:11][C:6]([O:5][CH2:4][CH2:3][CH2:2][N:22]3[CH2:23][CH2:24][CH2:25][CH:21]3[CH3:20])=[CH:7][CH:8]=2)[CH2:13][CH2:14]1

Participants

Procedure

A A mixture of trans-4-[4-(3-chloropropoxy)phenyl]cyclohexanol (403 mg), sodium hydrogenocarbonate (252 mg) potassium iodide (10 mg) and 2-methylpyrrolidine (153 mg) in acetonitrile (10 mL) is heated for 24 hours under reflux, then concentrated under reduced pressure. The residue is dissolved in ethyl acetate (25 mL). The organic phase is washed with water (5 mL), dried over magnesium sulfate, concentrated under reduced pressure and purified by chromatography over silica gel (eluent dichloromethane/methanol from 98/2 to 90/10). Fractions containing the expected product are pooled and concentrated under reduced pressure to give 120 mg of 1-{3-[trans-4-(4-hydroxycyclohexyl)phenoxy]propyl}-2-methylpyrrolidine as a white solid melting at 80° C.