4-Methylmorpholine → N-[3-(4-Chlorophenyl)-2-phenyl-1-methylpropyl]-1-phenylcyclopentanecarboxamide

Participants

Reaction Steps

To a solution of phenylcyclopentanecarboxylic acid (Aldrich, 23 mg, 0.12 mmol) in methylene chloride (1 mL) at 0° C. was added a drop of dimethylformamide and oxalyl chloride (0.025 mL, 0.29 mmol). After stirring at room temperature for 1 h, the reaction mixture was concentrated on a rotary evaporator and dried under vacuum, and the resulting crude acyl chloride was used without further purification. The crude acyl chloride was dissolved in 1 mL of methylene chloride and was added to a suspension of N-[3-(4-chlorophenyl)-2-phenyl-1-methylpropyl]-amine hydrochloride (Reference Example 2) (diastereomer α, 30 mg, 0.10 mmol) and N-methylmorpholine (0.053 mL, 0.48 mmol) in 1 mL of methylene chloride. After stirring at room temperature overnight, the reaction mixture was loaded onto a silica gel column, which was eluted with 10% ethyl acetate to give the title compound. 1H NMR (400 MHz, CD3OD): δ 7.45 (d, 2H), 7.35-7.08 (m, 6 H), 6.97 (d, 2H) 6.90 (d, 2H), 6.59 (d, 2H), 4.19 (m, 1H), 2.74-2.45 (m, 5), 2.12-1.65 (m, 6H), 0.79 (d, 3H). LC-MS: m/e 432 (M+H)+ (4.4 min).

Provenance & Evidence