1,5-Dibromopentane → HCID 19734240, compound

Participants

Reaction Steps

4 g of 3-aminomethyl-3,4,5,6-tetrahydro-6-oxo-1H-azepino[5,4,3-Cd]indole hydrate (for preparation see Example 1C) were dissolved in 40 ml of dimethylformamide. 2.6 ml of triethylamine were added to the solution and subsequently, while stirring at room temperature, 2 4 ml of 1,5-dibromopentane were added. The reaction mixture was heated at 50° C. for 3.5 hours. The reaction mixture was worked up by evaporating it under reduced pressure (water pump vacuum) and taking up the residue in a 9:1 dichloromethane/methanol mixture. Then saturated aqueous sodium carbonate solution was added until pH 11 was reached. The organic phase was separated and the aqueous phase was washed twice more with 50 ml portions of the dichloromethane/methanol mixture. The combined organic phases were dried over sodium sulfate, filtered and evaporated. The residue was dissolved in ethanol, and diethyl ether was added to the solution until a slight turbidity appeared. The resulting crystals were filtered out and dried. 3.5 g of crystalline 3-(1-piperidinylmethyl)-3,4,5,6-tetrahydro-6-oxo-1H-azepino[5,4,3-cd]indole were obtained with a melting point of 119° to 122° C.

Provenance & Evidence