Sodium Hydroxide → 5-Bromospiro[indoline-3,4'-piperidin]-2-one

Participants

Reaction Conditions

Reaction Steps

5-Bromo-1,2-dihydro-2-oxospiro[3H-indole-3,4′-piperidine]-1′-cyano 12 (3.3 g, 10.8 mmol) was suspended in ethylene glycol (10 ml). The mixture was treated in NaOH (1.8 g, 45 mmol) and heated to 130° C. for 15 min. It was diluted with methylene chloride (500 ml) and washed with 10% aqueous K2CO3 (2×100 m). The organic layer was dried (Na2SO4) and concentrated and residue purified by silica gel chromatography (30% MeOH/CH2Cl2) to gave 13 as a light ceramic white solid 1.8 g (60%), mp 256-258° C. 1HNMR (DMSO-d6, 400 MHz) δ 10.6 (br s, 1H, NH), 7.57 (d, J=1.84 Hz, 1H), 7.36 (d, J=8.2 Hz, 1H), 6.79 (d, J=8.2 Hz, 1H), 4.05 (br s, 1H, NH), 3.06 (m, 2H), 2.84 (m, 2H), 1.64 (m, 2H), 1.55 (m, 2H), 13C NMR (DMSO-d6, 100 MHz) δ 180.93, 140.64, 137.98, 130.42, 126.75, 113.20, 111.45, 46.24, 40.92, 32.94. Anal. Calcd for C12H13BrN2O: C, 51.26; H, 4.66; N, 9.9. Found: C, 50.87; H, 4.91; N, 9.67.

Provenance & Evidence