Sodium Carbonate → HCID 70064159, compound

Participants

Reaction Steps

2-Methyl-4-(3-methoxyphenyl)-N-n-propylpyrrolidine (cis and trans mixture 85: 15, 920 mg, 3.95 mmol) was dissolved in 47% hydrobromic acid (20 mL) and heated at reflux temperature for 1.5 hours. The mixture was made alkaline by the addition of 10% sodium carbonate (75 mL) and the product extracted with diethyl ether and ethyl acetate (1:1,3×20 mL). Drying (MgSO4) afforded 840 mg of the crude product as a white solid. Chromatography on a SiO2HPLC column yielded 601 mg of the title compound.: m.p. 123°-24° C.; MS (EI) m/e calc'd for C14H21NO: 219.162, found 219.163; 219.15 (10, M+), 204.05 (47), 191.05 (14), 190.05 (100), 161.05 (6), 133.05 (6), 106.95 (8), 90.95 (6), 84.05 (12).

Provenance & Evidence