Potassium Hydroxide → HCID 54065698, compound

Participants

Reaction Steps

A stirred mixture of 3-(3-pyridyl)propionaldehyde (4.40 g, 32.5 mmoles) and 3-phenylpropylamine (5.30 g, 1.2 equiv.) in methanol at rt was treated with sodium cyanoborohydride (1 g, 0.5 equiv.). After 1 h at rt the mixture was further treated with solid potassium hydroxide (3.6 g, 2 equiv.) and stirring was continued for 2 h. The resulting mixture was partitioned between brine and ether. The aqueous layer was extracted with ether and the combined ether extracts were extracted with 6N HCl (3×). These aqueous extracts were basified with solid potassium hydroxide and extracted with ether (3×), dried over sodium sulfate and concentrated in vacuo. The residue was distilled under high vacuum to give the product as a colorless oil (2.44 g, 30%), b.p. ca. 162° C./0.5 mm Hg.

Provenance & Evidence