Sodium Bicarbonate → HCID 22236594, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 4-methyl-1,2,3,4,5,6-hexahydro-benzo[e][1,4]diazocine (1.2 g, 6.8 mmole) in hydrochloric acid (2 N, 30 mL) cooled to 0° C. was added sodium nitrite (0.9 g, 13 mmole) in water (5 mL). The mixture was stirred for 1 hour at 0° C. and then neutralized with solid sodium bicarbonate and extracted with ethyl acetate (3×100 mL). The combined organic layers were washed with saturated aqueous sodium chloride (200 mL), dried and concentrated to a light brown oil. This oil was redissolved in THF (50 mL) and added to a suspension of lithium aluminum hydride (1.0 g, 25 mmole) in THF (50 mL) and the mixture refluxed for 3 hours under nitrogen. The excess hydride was destroyed at 0° C. by the cautious addition of water. The mixture was diluted with THF (200 mL) and filtered. Evaporation of the filtrate in vacuo provided 1.4 g of the title compound as a light yellow oil.

Provenance & Evidence