Triethylamine → N-methyloxan-4-amine hydrochloride

Participants

Reaction Conditions

Reaction Steps

A mixture of methylamine hydrochloride (5.4 g), terahydro-4H-pyran-4-one (8 g), triethylamine (2.4 g), 5% palladium on carbon (400 mg) and methanol (56 ml) were stirred at 60° C. for 3 hours under a hydrogen atmosphere. The palladium on carbon was removed by filtration through diatomaceous earth (Celite®) and the resultant filtrate evaporated in vacuo to a cream solid. To this solid were added propan-2-ol (39 ml), methanol (10 ml) and diethyl ether (20 ml), the resultant suspension then allowed to stir at room temperature for 1 hour, the solid was collected by filtration, washed with diethyl ether (10 ml) and dried in vacuo at room temperature to give N-methyl-N-(tetrahydropyran-4-yl)amine hydrochloride (9.83 g) as a white solid; NMR Spectrum: (DMSOd6) 1.62 (m, 2H); 1.94 (m, 2H); 2.53 (m, 3H); 3.14 (m, 1H); 3.3 (m, 2H); 3.91 (m, 2H); 9.24 (s, 2H).

Provenance & Evidence