Iodine → 9,10-dihydro-9-methyl-4-(1-methyl-4-piperidyl)-4H-benzo[4,5]cyclohepta[1,2-b]thiophen-4-ol

Participants

Reaction Steps

2.4 g of magnesium previously activated with iodine were reacted with 12.0 g of 4-chloro-1-methylpiperidine in 100 ml of anhydrous tetrahydrofuran over 2 hours at reflux temperature. The reaction mixture was cooled to 10°, and reacted with a solution of 9,10-dihydro-9-methyl4H-benzo[4,5]cyclohepta[1,2-b]thiophen-4-one in 70 ml of anhydrous tetrahydrofuran. After 1 hour of stirring at room temperature and 1 hour at reflux temperature the reaction mixture was cooled and treated with 150 ml of 20% w/v of aqueous ammonium chloride. The organic phase was separated off and worked up to give as a thick oil 9,10-dihydro-9-methyl-4-(1-methyl-4-piperidyl)-4H-benzo[4,5]cyclohepta[1,2-b]thiophen-4-ol which was further reacted as such.

Provenance & Evidence