HCID 18007303, compound → HCID 18007284, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of N-benzyl-3-methoxy-6,7,8,9-tetrahydro-5H-benzocyclohepten-6-amine (3.0 g) and 47% hydrobromic acid (106 ml) was stirred at 130° C. for 1.5 hours. After cooling, the reaction mixture was concentrated in vacuo. To the residue was added 28% ammonium hydroxide, and the whole was extracted once with ethyl acetate. The extract was washed twice with brine, dried over anhydrous sodium sulfate, and concentrated in vacuo. The residue was purified by column chromatography on silica gel (gradient elution; chloroform-methanol; 25:1 to 15:1) to give 8-benzylamino-6,7,8,9-tetrahydro-5H-benzocyclohepten-2-ol (1.9 g) as an oil, which solidified on standing.

Provenance & Evidence