Benzyl Bromide → 1-benzylindoline

Participants

Reaction Steps

A solution of 5 g (41.96 mmol) of indoline in DMF was treated with 5.8 g (41.96 mmol) of K2CO3 and then at 0° C. dropwise, under intense stirring, with 5.5 mL (46.2 mmol) of benzylbromide. The mixture was stirred at RT for 10 hrs and then for 2 hrs at 60° C. The resulting thick pulp was distributed between a saturated aqueous solution of NH4Cl and Et2O. Drying of the combined organic phases over Na2SO4 and evaporation of the solvent yielded 6.1 g (69%) of N-benzylindoline MS: 210 (MH+).

Provenance & Evidence