Hydrogen Bromide → HCID 20353218, compound

Participants

Reaction Steps

A solution of 5.0 g (14.55 mmoles) of 5-amino-2-cyclopentylmethyl-2,3,8,12b-tetrahydro-1H-3a,8-methanodibenzo[3,4:6,7]cyclohepta[1,2-c]pyrrole, (Example 64), in 25 ml of 40% hydrobromic acid, cooled at 5°, was diazotized with a solution of 1.1 g (16 mmoles) of sodium nitrite in 5 ml of water. The reaction mixture was allowed to warm to room temperature, filtered, and then added dropwise to a solution of 4.0 g (27.7 mmoles) of cuprous bromide in 25 ml of 48% hydrobromic acid. After standing overnight, dilution with water gave a precipitate which was collected by filtration. The solids were extracted with methylene chloride, and the organic layer washed with 1N aqueous sodium hydroxide solution was then with water. The extract was dried over potassium carbonate and evaporated to give 1.2 g of 5-bromo-2-cyclopentylmethyl-2,3,8,12b-tetrahydro-1H-3a,8-methanodibenzo[3,4:6,7]-cyclohepta[1,2-c]pyrrole as an oil; nmr spectrum δ 1.0-4.0 (m, 19); 6.8-7.5 (m, 7).

Provenance & Evidence