Dichloromethane → HCID 70131009, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of N-((R)-1-phenylethyl)-((6R)-3-hydroxy-6,7,8,9-tetrahydro-5H-benzocyclohepten-6-yl)amine-hydrobromide (7.67 g), ethyl bromoacetate (3.8 ml), potassium carbonate (17.6 g), and tetrabutylammonium chloride (1.18 g) in a mixture of dichloromethane (80 ml) and water (40 ml) was refluxed for 9 hours. After separation, the organic layer was washed with water and brine, dried over anhydrous magnesium sulfate, and evaporated in vacuo. The residue was dissolved in ethyl acetate (90 ml). To the solution was added 4N hydrogen chloride in ethyl acetate (5.6 ml), and the mixture was stirred at 5° C. for 1 hour. The precipitate was collected, washed with a little amount of ice-cold ethyl acetate, and dried under reduce pressure to afford N-((R)-1-phenylethyl)-((6R)-3-ethoxycarbonylmethoxy-6,7,8,9-tetrahydro-5H-benzocyclohepten-6-yl)amine hydrochloride (4.99 g).

Provenance & Evidence