Benzylamine → 6-heptynoic acid N-benzylamide

Participants

Reaction Steps

1-(3-dimethylaminopropyl)-3-ethylcarbodiimide (3.3 g, 17.4 mmol) was added to a mixture of 6-heptynoic acid (1.1 g, 8.7 mmol), benzylamine (950 μl, 8.7 mmol), 1-hydroxybenzotriazole (1.2 g, 8.7 mmol) and triethylamine (2.4 ml, 17.4 mmol) in tetrahydrofuran (25 ml) and the mixture was stirred at room temperature for 16 hours. The reaction was diluted with sodium hydrogen carbonate (sat, 60 ml) and extracted with ethyl acetate (2×100 ml). The extracts were washed with brine, dried (MgSO4) and evaporated in vacuo to provide 6-heptynoic acid N-benzylamide as a brown solid (2.1 g, 99%). (ES+) 216 ([MH]+).

Provenance & Evidence