1H-Isoindole-1,3(2H)-dione, 2-(2-bromoethyl)- → Ammonia

Participants

Reaction Steps

6-Butyl-8-(4-piperidinyloxy)quinoline (for example, as prepared for Intermediate 4) (2.44 g, 8.59 mmol) was stirred with 2-(2-bromoethyl)-1H-isoindole-1,3(2H)-dione (commercially available, for example, from Acros and/or Aldrich) (2.40 g, 9.4 mmol) and potassium carbonate (5.9 g, 43 mmol) in 2-butanone (75 ml) under nitrogen at 80° C. for 3 days. Further 2-(2-bromoethyl)-1H-isoindole-1,3(2H)-dione (2.4 g, 9.4 mmol) was added and the heating and stirring were continued for a further 24 h. More 2-(2-bromoethyl)-1H-isoindole-1,3(2H)-dione (1.2 g, 4.7 mmol) was added and the heating and stirring were continued for a further 24 h. The mixture was cooled and partitioned between water and DCM. The aqueous layer was extracted with more DCM (×2) and the combined organic layers were washed with water, dried (MgSO4) and evaporated to an oil. This oil was re-dissolved in DCM and loaded onto a column of silica gel (250 g) that had been preconditioned with DCM. The column was eluted with DCM, then DCM-ethanol-0.88 s.g. aqueous ammonia solution (200:8:1) to give the title compound (2.76 g, 6.03 mmol). LCMS RT=2.91 min, ES+ve m/z 458 [M+H]+.

Provenance & Evidence