Water → HCID 19734231, compound

Participants

Reaction Steps

6.2 g of 3-benzylaminomethyl-3,4,5,6-tetrahydro-6-oxo-1H-azepino[5,4,3-cd]indole (see Example 2 for preparation) were dissolved in 250 ml of dimethylformamide. 0.81 ml of methyl iodide and 1.81 g of potassium carbonate were added to the stirred solution at room temperature. The reaction mixture was stirred at room temperature for 3 hours. Subsequently, to work up, the dimethylformamide was stripped off under reduced pressure (oil pump vacuum) at 50° C. The remaining oily residue was taken up in a mixture of equal parts of water and dichloromethane, the dichloromethane phase was separated, and the aqueous phase was extracted twice more with dichloromethane. The organic phases were combined, dried over sodium sulfate, filtered and evaporated. 3.84 g of oily crude product remained as residue. This was purified by chromatography under moderately elevated pressure (=low pressure chromatography =LPLC under 3 to 6 bar) on silica gel (proprietary product LiChroprep® Si 60) using dichloromethane/methanol 9:1 as eluent. 3.26 g of oily 3-(N-benzyl-N-methylaminomethyl)-3,4,5,6-tetrahydro-6-oxo-1H-azepino[5,4,3-cd]indole were obtained.

Provenance & Evidence