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

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.

1. temperatureThe reaction mixture was heated
2. temperatureunder reflux for 16 hours
3. customthe solvent was removed under reduced pressure
4. customThe residue was partitioned between dichloromethane (50 ml) and water (50 ml)
5. dry with materialThe organic layer was dried over anhydrous magnesium sulphate
6. customthe solvent was removed under reduced pressure
7. dissolutionThe crude residue was dissolved in tetrahydrofuran (30 ml)
8. temperatureThe reaction mixture was heated
9. temperatureunder reflux for 2 hours
10. filtrationThe suspension was filtered
11. concentrationthe liquid was concentrated under reduced pressure

ORD record

ord-9c478ebcafd64da8838061055e876009

Source dataset

uspto-grants-2007_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07238676B2