Sodium Bicarbonate → 7-chloro-4-methyl-3,4,5,6-tetrahydro-2H-benzo[e][1,4]diazocin-1-ylamine

Participants

Reaction Steps

To a solution of 7-chloro-4-methyl-1,2,3,4,5,6-hexahydro-benzo[e][1,4]diazocine (4.0 g, 0.021 mole approximately) in hydrochloric acid (2 N, 100 mL) cooled to 0° C. was added sodium nitrite (2.5 g, 0.036 mole) in water (20 mL). The mixture was stirred for 1 hour and treated with sodium bicarbonate and extracted with ethyl acetate (3×100 mL). The combined organic layers were washed with saturated sodium chloride (200 mL), dried and concentrated to a light brown oil. The oil was redissolved in THF (50 mL) and added to a suspension of lithium aluminum hydride (2.5 g, 0.063 mole) in THF (100 mL) and the mixture refluxed for 3 hours. 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 3.5 g of the title compound as a light yellow oil. This oil was used for indole formation without further purification. MS (ES) m/z 226.5 ([M+H]+).

Provenance & Evidence