Dichloromethane → Bis(cyclopropylmethyl)amine

Participants

Reaction Steps

To a suspension (3-{[(3,5-bistrifluoromethyl-benzyl)-(2H-tetrazol-5-yl)-amino]-methyl}-8-methyl-quinolin-2-yl)-bis-cyclopropylmethyl-amine (0.132 g, 0.224 mmol) in water (2 mL), sodium hydroxide (0.018 g, 0.448 mmol) was added and stirred for 15 min at RT followed by the addition of dichloromethane (2 mL). To this reaction mixture, dimethyl sulphate (0.032 g, 0.26 mmol) was added followed by the addition of tetra butyl ammonium bromide (0.003 g, 0.011 mmol). The reaction was stirred for 1 h. The organic layer was separated from aqueous layer and the aqueous layer was extracted with DCM (3×10 mL), the combined organic layer was washed with brine, dried over sodium sulphate and then concentrated under vacuum to afford the crude residue which was purified by column chromatography over 100-200 mesh silica gel using 8% ethyl acetate and petroleum ether to afford (3-{[3,5-bis-trifluoromethyl-benzyl)-(2-methyl-2H-tetrazole-5-yl)-amino]-methyl-}-8-methyl-quinoline-2-yl)-bis-cyclopropylmethyl-amine (0.07 g, 52%).

Provenance & Evidence