2-Phenylcyclohexanone → HCID 68735476, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 2-phenylcyclohexanone (1.74 g, 9.99 mmol), (R)-2-methylpiperazine (3.00 g, 30.0 mmol) and titanium (4+) isopropoxide (5.85 ml, 20.0 mmol) was heated at 80° C. under N2 overnight. After cooling to rt, 10 mL of MeOH was added followed by slow addition of NaBH4 (1.13 g, 30.0 mmol). After stirring for 30 min, the solvent was evaporated and the residue was redissolved in EtOAc. The solution was treated with 15 g of NaHCO3 and 1 mL of water to generate slurry. This was filtered with large excess of EtOAc. The solvent was evaporated and the residue was submitted to flash chromatography (SiO2, DCM to DCM/MeOH=100:5 to 100:10 to 100:20) to give (3R)-3-methyl-1-(2-phenylcyclohexyl)-piperazine (1.82 g, 70.5% yield) as a colorless oil.

Provenance & Evidence