Methanol → Methyl 1-amino-1-cyclopentanecarboxylate, HCl

Participants

Reaction Conditions

Reaction Steps

Preparation of methyl-1-N,N-dichloroamino-1-cyclopentanecarboxylate: To 30 ml of absolute methanol at 0° C, there was added dropwise with stirring over 0.5 hr. 7.9 ml of freshly distilled thionyl chloride. When the addition of thionyl chloride was completed, 12.9 g (0.1 mol) 1-amino-1-cyclopentanecarboxylic acid was added in portions over 0.25 hr. The suspension was heated with stirring, and the temperature maintained at 75° C for 2.5 hr. after solution of the reaction suspension. Removal of the methanol under reduced pressure gave an off-white crystalline mass. Trituration of this material with anhydrous ether gave 16.1 g (0.09 mol), 90%, methyl-1-amino-1-cyclopentanecarboxylate hydrochloride, mp 205°-207° C acetone:hexane, Kr (KBr) 1740 (C=O) cm-1 ; pmr (D2O) δ 3.95 (s, 3H) and 2.83 - 1.66 (m, 8H) ppm.

Provenance & Evidence