Cyclopentylamine → N-(2-Chloro-4-pyridinyl)-N′-cyclopentylurea

Participants

Reaction Steps

A stirred solution of 3.5 grams (0.0141 mole) of phenyl N-(2-chloro-4-pyridinyl)carbamate and 1.7 ml (0.0172 mole) of cyclopentylamine in 60 ml of acetone was heated under reflux for three hours. The reaction mixture was cooled and concentrated under reduced pressure to a residual oil. The oil was dissolved in 20 ml of methylene chloride and passed through a column of silica gel. Elution was accomplished with 5% and 10% acetone-methylene chloride. The appropriate fractions were combined and concentrated under reduced pressure to yield 2.9 grams of N-(2-chloro-4-pyridinyl)-N'-cyclopentylurea; m.p. 119°-121° C. The nmr spectrum was consistent with the proposed structure.

Provenance & Evidence