Benzyl Bromide → HCID 10293520, compound

Participants

Reaction Steps

To a solution of 7,8-dimethoxy-1-phenyl-3,5-dihydro-4H-2,3-benzodiazepin-4-one VIaa (100 mg, 0.34 mmol) in DMF (5 ml), under an inert atmosphere, add NaH in oil (12 mg, 0.30 mmol). Then add dropwise benzyl bromide (40 μl, 0.34 mmol). After 2 hours at room temperature, evaporate the DMF. Take up the residue in CH2Cl2, wash twice with water. Dry the organic phases on Na2SO4. Purify by silica gel column chromatography (AcOEt/hexane, 4:1). Yield: 71%. M: 114–116° C. 1H-NMR (200 MHz, CDCl3): d 3.53–3.64 (m, 2H, CH2), 3.73 (s, 3H, OCH3), 4.00 (s, 3H, OCH3), 4.93–5.32 (d, 2H, NCH2Ph), 6.63 (s, 1H, Ar), 6.92 (s, 1H, Ar), 7.20–7.59 (m, 10H, Ar).

Provenance & Evidence