Diethyl Ether → Ethyl 4-aminocyclohexanecarboxylate

Participants

Reaction Steps

To a suspension of 4-amino-cyclohexanecarboxylic acid (G) (5 g, 35 mmol) in EtOH (175 mL) at 0° C. was added SOCl2 (12.6 mL, 174 mmol) dropwise via a syringe. The reaction mixture was warmed to room temperature and stirred for 16 h. After concentration of the reaction mixture, ether was added and the suspension was filtered to give 4-amino-cyclohexanecarboxylic acid ethyl ester (H) (mixture of cis/trans) as a white solid (4.8 g): 1H NMR (300 MHz, CDCl3) δ8.35 (br s, 3 H), 4.18 (m, 2 H), 3.36-3.15 (m, 1 H), 2.54 (m, 1 H), 2.30-1.45 (series of m, 8 H), 1.13 (t, 3 H); mass spectrum m/z 172 [(M+H)+; calcd for C9H18NO2: 172].

Provenance & Evidence