1,3-Propanediamine → HCID 21998658, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 4-cyano-4-phenylcyclohexanone (5.0 g, 25.09 mmol) and 1,3-diaminopropane (5.58 g, 75.3 mmol) and p-toluenesulfonic acid (23 mg) in benzene (50 mL) was refluxed for 4 h in Dean-Stark trap to remove the water that formed. Solvent was evaporated and the residue was redissolved in methanol (40 mL) and cooled to 0° C. To this, sodium borohydride (6.4 5 g) was added in portions and the mixture was stirred at room temperature for 3 h. Solvent was evaporated, the residue was dissolved in dichloromethane (300 mL), washed with brine (3×500 mL), dried (potassium carbonate), and the solvent evaporated to leave the product as a pale yellow viscous oil (4.5 g, 72%). The 1H-NMR showed this product to be pure and found to contain the cis/trans isomers in the ratio of about 4:1.

Provenance & Evidence