3,3-Dimethylbutylamine → HCID 22992905, compound

Participants

Reaction Steps

A solution of methyl 4-cyanobenzoic acid (1, 735 mg, 5.0 mmol) in 12 mL of DMF under argon at room temperature was treated 3,3-dimethylbutylamine (2, 505 mg, 5.0 mmol), ethyl-3-(3-dimethylamino)-propyl carbodiimide hydrochloride (1.5 g, 5.0 mmol) and hydroxybenzotriazole monohydrate (685 mg, 5.0 mmol) and stirred overnight. The reaction mixture was diluted with ethyl acetate and washed with 10 percent citric acid, water, dilute sodium bicarbonate, water and brine. The dried (anhydrous magnesium sulfate) organic fraction was concentrated to give 1.5 g. Flash chromatography on 150 mL of EM-60 silica gel, eluting with ethyl acetate/hexanes (1:4) gave the title compound (1.06 g, 92%), mp 154-157° C. Analysis calculated for C14H18N2O: C, 73.01; H, 7.88; N, 12.16. Found: C, 73.00; H, 7.92; N, 12.17.

Provenance & Evidence