Hydrochloric Acid → HCID 13450868, compound

Participants

Reaction Steps

A mixture of 9-nitro-3,4,5,6-tetrahydro-2H-1,5-methano-1,4-benzodiazocine (17.5 g.), allyl bromide (7.6 ml.), sodium bicarbonate (1 teaspoon) and N,N-dimethylformamide (200 ml.) was stirred overnight at room temperature, then concentrated to dryness. The residue was partitioned between dilute aqueous sodium hydroxide and isopropyl acetate. The isopropyl acetate layer was washed with dilute aqueous sodium hydroxide and brine, filtered and concentrated to dryness. The residue was recrystallized from isopropyl alcohol, and the product was combined with corresponding product (2.3 g.) from a previous a preparation. Ethereal hydrogen chloride was added to a solution of the combined products in ethyl acetate affording 4-allyl-9-nitro-3,4,5,6-tetrahydro-2H-1,5-methano-1,4-benzodiazocine (10 g.), the compound of Formula IV wherein Q is allyl.

Provenance & Evidence