Cysteamine Hydrochloride → 2-{[(Pyridin-3-yl)methyl]sulfanyl}ethan-1-amine

Participants

Reaction Steps

16.8 g of sodium hydroxide was dissolved in 350 ml of ethanol and 17.2 g of 3-chloromethylpyridine hydrochloride and 23.7 g of 2-mercaptoethanamine hydrochloride were added with ice bath cooling. The reaction mixture was allowed to warm to room temperature over 2 hours, was concentrated, diluted with water, and extracted with 3×100 ml of dichloromethane. The combined organic layers were washed with saturated brine, dried over potassium carbonate and concentrated. The residue was distilled to give 12.30 g (70%) of 2-[[(3-pyridyl)methyl]thio]ethanamine, bp 115°-125° C./0.1 mm.

Provenance & Evidence