Hydrazine hydrate (1:1) → alpha-Methylcyclohexaneethanamine

Participants

Reaction Steps

To a suspension of (±)-N-(2-cyclohexyl-1-methylethyl)-2-phthalimidoacetamide (12.0 g, 36.7mmol) in ethanol (180 ml) was added hydrazine hydrate (2.05 g, 40.3 mmol) and the mixture heated under reflux for 1.5 hours. After cooling and standing at 0° for 24 hours, the slurry was filtered and the residue washed with petrol (40°-60°). The combined filtrateswere evaporated to dryness and the oily residue triturated with petrol (3×100 ml). The combined extracts were evaporated to dryness to givea colourless oil. The oil was dissolved in ether (50 ml) and the solution added to a warm solution of fumaric acid (2.7 g) in ethanol (50 ml). On standing, a colourless solid was deposited, m.p. 132°-134° C.

Provenance & Evidence