Triethylamine → HCID 19097478, compound

Participants

Reaction Steps

A solution of 1,2,3,4-tetramethyl-3-piperidineethanamine (2.9 g, I6 mmol), triethylamine (10 mL) and methylene chloride (25 mL) was cooled to 0° C. and 3-thiophenecarboxylic acid chloride (2.3 g, 16 mmol) in methylene chloride (15 mL) was added. The reaction mixture was warmed to room temperature and stirred for 16 hours. The reaction mixture was diluted with ether (200 mL) and washed with saturated sodium bicarbonate (2×50 mL), water (50 mL), then brine (50 mL). The organic layer was separated, dried over Na2SO4 and treated with charcoal. The solvent was removed in vacuo and the residue was purified by column chromatography on silica eluting with ether (100%), then 2% diisopropylamine/ether, followed by 5% isopropylamine/ether to afford 2.9 g (62%) of N-[2-(1,2,3,4-tetramethyl-3-piperidinyl)-ethyl]-3-thiophenecarboxamide as an oil. The product was dissolved in ethanol (7 mL), cooled to 0° C., treated with 3.2N ethanolic HCl and diluted with ether to afford 3.1 g of the hydrochloride salt as a yellow solid. The salt was recrystallized from ethanol/ether and had a melting point of 228°-229° C.

Provenance & Evidence