Dimethylamine → HCID 10608272, compound

Participants

Reaction Steps

A 37% aqueous solution of formaldehyde (11 g, 0.176 mol) was added dropwise to 10 g (0.068 mol) of 5-methoxy-1H-indole and 17 mL (0.176 mol) of 40% aqueous dimethylamine in 100 mL of tetrahydrofuran and the mixture heated to maintain reflux for 3 hours. After cooling water was added and the mixture extracted with EtOAc. The EtOAc solution was washed twice with water, dried (Na2SO4), and concentrated at reduced pressure. The residue was chromatographed on silica eluting with a gradient, CH2Cl2→2% MeOH/CH2Cl2, to give 6.26 g (45% yield) of 1-dimethylaminomethyl-5-methoxy-1H-indole as an oil.

Provenance & Evidence