Hydrochloric Acid → HCID 9926899, compound

Participants

Reaction Steps

To 6.31 g (21.4 mmol) of N-(1-azabicyclo[3.3.0]octan-5-yl)methyl-N-methyl-1,4-diaminonaphthalene, water (27.5 ml) and concentrated sulfuric acid (55 ml) were added to dissolve the compound therein. Sodium nitrite (1.40 g, 20.3 mmol) in water (8 ml) was added dropwise to the solution at a temperature of -5+ C. and then stirred for 15 minutes. Cuprous chloride (8.50 g, 85.9 mmol) suspended in concentric hydrochloric acid (18 ml) was added dropwise into the solution which was kept at 85° C. under stirring condition. After further stirring for 5 minutes, the reaction mixture was cooled by water with ice pieces. Several ice pieces were added to the reaction mixture which was made alkaline by adding 10% aqueous sodium hydroxide solution and extracted by chloroform. The resulting organic layer was dried over anhydrous sodium sulfate, concentrated in vacuo, purified by column chromatography to afford the desired compound (950 mg, 14.1% ), as a colorless liquid.

Provenance & Evidence