Hydrochloric Acid → HCID 20353247, compound

Participants

Reaction Steps

To a suspension of 5.0 g (37.39 mmoles) of aluminum chloride in 75 ml of methylene chloride, cooled to 0°, was added dropwise 3.0 g (38.2 mmoles) of acetyl chloride. Then 5.0 g (13.7 mmoles) of 2-cyclopentylmethyl-2,3,8,12b-tetrahydro1H-3a,8methanodibenzo[3,4:6,7]cyclohepta[1,2-c]pyrrole was added portionwise. The reaction mixture was heated at reflux for several hours and then poured into 1N aqueous hydrochloric acid. The product was extracted with methylene chloride, and the extracts were washed with water, with 1N aqueous sodium hydroxide, with water and dried over potassium carbonate. The solvent was evaporated to leave 5.6 g of 5-acetyl-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); 2.5 (s, 3); 7.1-7.25 (m, 5); 7.7-7.9 (m, 2). The 220MHz nmr spectrum showed that the product contained approximately 83% of the 5-acetyl isomer. A sample was purified by crystallization of the trifluoroacetate salt from ether/ethyl acetate and then of the hydrochloride salt from acetone, mp, 160-172° (dec.); ir. 1700 cm-1 (COCH3).

Provenance & Evidence