Acetic Acid → N,N-Diethyl-1-heptanamine

Participants

Reaction Steps

Dissolve 50.90 ml (0.5 moles) diethylamine and 57.10 g (0.5 mole) heptaldehyde in 500 ml methanol and stir at room temperature for one hour. Slowly add 31.42 g sodium cyanoborohydride in 500 ml methanol to the stirred reaction mixture. Add glacial acetic acid to the reaction mixture until pH=6. Stir at room temperature overnight. Concentrate reaction mixture volume to 300 ml and then add 500 ml distilled water. Add concentrated hydrochloric acid until pH=1. Extract with 5×250 ml methylene chloride. Evaporate organic solvent and then dissolve the residue in 400 ml 0.1N HCl. Wash aqueous solution with 3×200 ml diethyl ether and then add 2N NaOH until solution is basic (pH=12). Extract with 3×200 ml diethyl ether. Dry over MgSO4, filter and evaporate, the distill in vacuo to obtain 46.0 g (53.7%) title compound.

Provenance & Evidence