Hydrochloric Acid → HCID 19734265, compound

Participants

Reaction Conditions

Reaction Steps

2 ml of trimethylsilyl iodide were added to a mixture of 1.5 g of 3-[N-(4-methoxybenzyl)aminomethyl]-3,4,5,6-tetrahydro-6-oxo-1H-azepino[5,4,3-cd]indole (see Example 21 for preparation) and 2.5 g of 1,4-diazabicyclo[2.2.2]octane (=DABCO). The reaction mixture was heated at 150° C. under a nitrogen atmosphere for 24 hours. The reaction mixture was cooled to room temperature and then diluted with 25 ml of methanol and acidified with 20% strength aqueous hydrochloric acid. The mixture was then vigorously stirred at room temperature for 2 hours. To work up the reaction mixture it was diluted with 30 ml of water, the aqueous phase was separated and the organic phase was washed twice more with 20 ml portions of water. The combined aqueous phases were neutralized with dilute sodium hydroxide solution and subsequently evaporated under reduced pressure (water pump vacuum). The crude product which remained as an oily residue was purified by chromatography on silica gel under slightly elevated pressure (flash chromatography) using methanol/25% strength aqueous ammonia solution 98:2 as eluent. 0.6 g of 3-[N-(4-hydroxybenzyl)aminomethyl] 3,4,5,6-tetrahydro-6-oxo-1H-azepino(5,4,3-cd]indole was obtained as an oil.

Provenance & Evidence