Potassium Hydroxide → 2287238-27-9

Participants

Reaction Steps

A mixture of racemic cis (1-benzyl-4-methyl-piperidin-3-yl)-carbamic acid methyl ester (1.56 g, 5.95 mmol) and potassium hydroxide (9.90 mL, 59.5 mmol, 6M solution) in methanol (50 mL) was heated at reflux for 48 hours. The cooled reaction mixture was diluted with water and extracted with ethyl acetate. The combined organic phases were washed with brine then dried over sodium sulfate and concentrated under vacuum. The resulting residue was purified by column chromatography on silica gel (gradient: 0 to 7% 2M NH3 in methanol solution in DCM) to afford 460 mg (38%) of racemic cis 1-benzyl-4-methyl-piperidin-3-ylamine. LCMS (Method H, ESI): RT=0.35 min, m+H=204.9; 1H NMR (400 MHz, CDCl3) δ: 7.29-7.28 (m, 5H), 3.45 (s, 2H), 2.76-2.72 (m, 3H), 2.20-2.11 (m, 1H), 1.97 (td, 1H), 1.42 (m, 5H), 0.91 (d, 3H).

Provenance & Evidence