Dipropargylamine → 2,4-Bis-benzyloxy-5-isopropenyl-N,N-di-prop-2-ynyl-benzamide

Participants

Reaction Steps

A stirred solution of 2,4-bis-benzyloxy-5-isopropenyl-benzoic acid (Example 1 Step 6) (1 equivalent) in dichloromethane (10 ml) was treated successively with N-ethyl-N′-(3-dimethylaminopropyl)carbodiimide hydrochloride (1.2 equivalents), 1-hydroxybenzotriazole (1.2 equivalents) and dipropargylamine (1.5 equivalents) and the mixture was stirred at room temperature overnight. The mixture was washed successively with 2M hydrochloric acid and 2M sodium hydroxide, the organic layer was separated and the solvent removed in vacuo to afford the product which was either obtained pure or was purified by column chromatography on silica (eluting with mixtures of ethyl acetate in petroleum ether or methanol in ethyl acetate as appropriate). MS: [M+H]+ 450

Provenance & Evidence