Triethylamine → Methyl 4-Thiomorpholinobutyrate

Participants

Reaction Steps

A mixture of 64.0 g. (0.28 mole) of methyl γ-iodobutyrate, 28.0 g. (0.28 mole) of triethylamine, 28.7 g. (0.28 mole) of thiomorpholine (J. Am. Chem. Soc. 76, 1187 (1954)) and 1 liter of benzene was stirred and heated at 60°-70°C. for 18 hours. After cooling the reaction mixture, the precipitated amine hydroiodide was removed by suction filtration. The benzene solution was evaporated to give a orange-red residue which was vacuum distilled (b.p. 84°-85°C. at 0.1 mm) to give 28.38 g. (50%) of the product as a colorless liquid.

Provenance & Evidence