Tert-Butylamine → HCID 89422917, compound

Participants

Reaction Steps

To a solution of 1-(4-(benzyloxy)-1-methyl-1H-indol-5-yl)butan-1-one (0.260 g, 0.85 mmol) in DCE (4 mL) was added t-BuNH2 (0.40 mL, 3.79 mmol). The mixture was cooled to 0° C. before TiCl4 solution (1M DCE, 0.55 mL, 0.55 mmol) was added dropwise via syringe pump over 30 min. The reaction was allowed to warm to room temperature and then heated at 50° C. for 6 h. The mixture was then diluted with DCM (15 mL) and quenched with NaHCO3 (aqueous saturated, 5 mL). Upon vigorous shaking, the organic phase was separated using a PTFE phase separator and dried over Na2SO4. Removal of the solvent afforded N-(1-(4-(benzyloxy)-1-methyl-1H-indol-5-yl)butylidene)-2-methylpropan-2-amine as a yellow oil, which was taken directly into next step without purification.

Provenance & Evidence