Cysteamine Hydrochloride → 2-{[(Pyridin-4-yl)methyl]sulfanyl}ethan-1-amine

Reaction equation

[OH-].[Na+].Cl.[SH:4][CH2:5][CH2:6][NH2:7].Cl.N1C=CC=CC=1.Cl[CH2:16][C:17]1[CH:22]=[CH:21][N:20]=[CH:19][CH:18]=1>C(O)C>[N:20]1[CH:21]=[CH:22][C:17]([CH2:16][S:4][CH2:5][CH2:6][NH2:7])=[CH:18][CH:19]=1

Participants

Procedure

34.1 g of sodium hydroxide was dissolved in 500 ml of ethanol under an argon atmosphere and 48.6 g of 2-mercaptoethanamine hydrochloride and 35 g of 4-chloromethylpyridine pyridine hydrochloride were added with ice bath cooling. The reaction mixture was allowed to warm to room temperature over 2 hours, was concentrated, diluted with 300 ml of water and was extracted with 3×150 ml of dichloromethane. The combined organic layers were washed with 100 ml of saturated brine, dried over potassium carbonate and were evaporated to a dark oil which was distilled. The fractions bp 120°-130° C./0.1 mm amounted to 30.68 g (85%) of 2-[[(4-pyridyl)methyl]thio]ethanamine.