Triethylamine → HCID 22346254, compound

Participants

Reaction Steps

tert-Butyl N-(2-aminoethyl)carbamate (5.00 g, 31.2 mmol) was dissolved in dry dichloromethane (50 mL). Triethylamine (7.02 g, 68.7 mmol) was added and the mixture was cooled in an ice bath, with stirring. 2-Chloroethanesulfonyl chloride (5.09 g, 31.2 mmol) was added dropwise, and the ice bath was removed. The mixture was stirred and allowed to warm to room temperature, stirring overnight. The mixture was partitioned between dichloromethane (150 mL) and 1.5M aqueous sodium carbonate solution (75 mL). The organic layer was dried (Na2SO4) and concentrated in vacuo to give the title compound (7.81 g, quantitative, contains 0.4 equivalents of triethylamine) as a colourless oil. δH (d6-DMSO) 6.53 (dd, 1H, J 16.6, 9.9 Hz), 6.24 (d, 1H, J 16.6 Hz), 5.95 (d, 1H, J 9.9 Hz), 5.06 (br s, 2H), 3.31-3.27 (m, 2H), 3.16-3.12 (m, 2H), 1.45 (s, 9H). LCMS (ES+) 251 (M+H)+.

Provenance & Evidence