Sodium Hydroxide → HCID 20353209, compound

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Reaction Steps

To a solution of 6.5 g (0.019 mole) 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 5ml of conc. hydrochloric acid and 120 ml of water, cooled to 0°, was added an ice cold solution of 1.5 g (.022 mole) of sodium nitrite in 5 ml of water over a 5 minute period. After stirring 10 minutes at 0°, an ice cold solution of 1.4 g (.022 mole) of sodium azide in 5 ml of water was added portionwise. A cream-colored precipitate formed followed by copious evolution of nitrogen. Stirring was continued for 1 hour at 0°. The reaction mixture was made basic (pH 13) with sodium hydroxide and allowed to stand overnight. It was dissolved in methylene chloride, the organic layer was separated, washed with water and dried over potassium carbonate. Evaporation of the solvent gave 4 g of the crude azide as a deep red oil. It was purified by chromatography on silica gel (5% methanol-chloroform) to give 5-azido-2-cyclopentylmethyl-2,3,8,12b-tetrahydro-1H-3a,8-methanodibenzo[3,4:6,7]cyclohepta[1,2-c]pyrrole; ir spectrum: strong --N=N=N absorption at 2100 cm-1.

Provenance & Evidence