Water → HCID 59442638, compound

Participants

Reaction Conditions

Reaction Steps

2.3 g of 4-(3-bromophenyl)-4-cyclopropylmethoxy-1-phenylcyclohexanecarbonitrile were suspended in 10 ml of ethylene glycol, 0.94 g of potassium hydroxide was added and the mixture was heated for 4 h at 195° C. The reaction mixture was then allowed to stand for 16 h at room temperature, poured onto 100 ml of water and adjusted to pH=3 with saturated aqueous sodium hydrogensulfate solution. The precipitated product was filtered off with suction and purified by preparative HPLC (column: Waters X-Terra MS C18 prep, 200×50 mm, 10 μm; eluent A: water+0.2% TFA, eluent B: acetonitrile; gradient and flow: 90% A+10% B and 50 ml/min for 2.2 min, then to 90% A+10% B and 150 ml/min in 1.3 min, then 90% A+10% B and 150 ml/min for 0.5 min, then to 80% A+20% B and 150 ml/min in 0.5 min, then to 5% A+95% B and 150 ml/min in 19.5 min, then 5% A+95% B and 150 ml/min for 6 min, then to 90% A+10% B and 150 ml/min in 1 min, then 90% A+10% B and 150 ml/min for 4 min). 215 mg of the title compound were obtained as a colorless oil.

Provenance & Evidence