Hydroxyacetonitrile → N1-Cyclohexyl-N1-(1,1-dimethylethyl)-1,2-ethanediamine

Participants

Reaction Steps

Hydroxyacetonitrile (5.3 ml of of a 70% w/w solution in water, 32 mmol) was added to a stirred solution of N-(tert-butyl)cyclohexanamine (5.3 ml, 32 mmol) in ethanol (50 ml) at room temperature. The reaction mixture was heated under reflux for 16 hours. The solution was allowed to cool to room temperature and the solvent was removed under reduced pressure. The residue was partitioned between dichloromethane (50 ml) and water (50 ml). The organic layer was dried over anhydrous magnesium sulphate and the solvent was removed under reduced pressure. The crude residue was dissolved in tetrahydrofuran (30 ml) and a solution of lithium aluminium hydride in tetrahydrofuran (1M, 55 ml, 55 mmol) was slowly added. The reaction mixture was heated under reflux for 2 hours. An aqueous solution of sodium hydroxide (2M, 6 ml) was then carefully added. The suspension was filtered and the liquid was concentrated under reduced pressure to give the title compound (3 g) as an oil.

Provenance & Evidence