Hydrochloric Acid → N,4,4-trimethylcyclohexan-1-amine

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Reaction Steps

To a solution of 4,4-dimethylcyclohexanone (25.2 g) in dry methanol under an atmosphere of nitrogen was added methylamine hydrochloride (13.2 g) and 3 Åmol sieves (1 g). The reaction mixture was stirred for 1 hr then sodium cyanoborohydride (12.7 g) added portionwise. The mixture was stirred for 17 hrs. A saturated solution of hydrogen chloride in methanol (200 ml) was added and the reaction mixture stirred for 1 hr the filtered through hyflo and concentrated in vacuo. The residue was partitioned between 1N sodium hydroxide (300 ml) and dichloromethane (200 ml). The layers were separated and the aqueous re-extracted with dichloromethane (2×200 ml). The combined organics were washed with saturated sodium hydrogen concentrated in vacuo. The residue was distilled under reduced pressure. Bpt 40°-45° C. at 0.1 mmHg. 1H NMR (CDCl s) δ0.92 (6H, s), 1.10-1.30 (5H, m), 1.30-1.50 (2H, m), 1.66-1.72 (2H, m), 2.26 (1H, m), 2.42 (3H, s).

Provenance & Evidence