N-Methylbenzylamine → HCID 54549073, compound

Participants

Reaction Steps

Oxalyl chloride (2.24 ml, 25 mmol) was added dropwise to a stirred solution of 5-bromoindole (5.0 g, 25 mmol) in anhydrous tetrahydrofuran (60 ml) under nitrogen at room temperature. After 2 hours the reaction mixture was ice-cooled and a solution of N-methylbenzylamine (10.8 g, 89 mmol) in anhydrous tetrahydrofuran (15 ml) added dropwise, then the resulting mixture was stirred for a further 2 hours at 0°-5° C. and partitioned between ethyl acetate and 2M hydrochloric acid. The organic phase was washed with 2M hydrochloric acid and then water, dried (Na2SO4) and evaporated under reduced pressure to give a solid which was triturated with a 1:2 mixture of hexane:ether, washed with ether (×3) and dried in vacuo, to afford the required product (7.02 g) as a solid. Rf 0.60 (SS 7). Found: C,57.65; H,4.02; N,7.50. C18H15BrN2O2 ; 0.33 H2O requires C,57.30; H,4.16; N,7.42%.

Provenance & Evidence