3-Methylbutanal → 2-Cyclopropylamino-4-methyl-pentanenitrile hydrochloride

Participants

Reaction Conditions

Reaction Steps

Following a procedure outlined in Synth. Commun. 15 (2), 1985, 157-163, 3-methylbutyraldehyde (2.0 g) and cyclopropylamine (0.81 mL) were combined and heated to 95° C. in a pressure tube for 2 minutes. The clear, yellowish solution was cooled to RT and trimethylsilyl cyanide (2.76 mL) was added carefully over 5 minutes. The mixture was re-heated to 100° C. for 2 minutes and then allowed to cool to RT. Methanol (12 mL) was added and the mixture was heated to reflux for 12 hours. The mixture was cooled, dissolved in ethyl acetate, washed with brine, dried over Na2SO4 and evaporated. The residue was treated with HCl in dioxane (approx. 0.7 M, 30 mL) and then with ether (60 mL) with stirring. After one hour, the precipitated white solid was filtered off and dried in vacuo (1.65 g). MS (ESI): 153.4 (MH+, free base).

Provenance & Evidence