Benzenesulfonyl chloride, 3,4-dichloro- → HCID 22220483, compound

Participants

Reaction Steps

To a stirred solution of 0.5 g (1.9 mmol) of the hydrochloride salt of 1-(4-amino-phenyl)-piperidine-4-one (which was obtained in Example 224) in 10 mL of anhydrous methylene chloride was added 0.99 mL (5.7 mmol) of diisopropylethyl amine. After 10 minutes of stirring, 0.51 g (2.1 mmol) of 3,4-dichlorobenzene sulfonyl chloride was added and the mixture was allowed to stir overnight. The reaction mixture was quenched with water and the solvent was removed in vacuo. The residue was dissolved in ethyl acetate and washed twice with water, twice with brine, dried over sodium sulfate and then concentrated in vacuo. The residue was then purified by flash chromatography (10% EtOAc in hexanes to 50% EtOAc in hexanes) and the title compound was collected as 0.25 g of a yellow solid; 1H NMR (300 MHz, CDCl3) δ 2.55 (t, J=6.09 Hz, 4H), 3.58 (t, J=6.03 Hz, 4H), 6.33 (s, 1H), 6.60-6.88 (m, 2H), 6.95-7.00 (m, 2H), 7.50 (d, J=1.47 Hz, 2H), 7.78-7.79 (m, 1H); MS (ES) m/z: 398.8 (MH+); HRMS found for C17H16Cl2N2O3S: 398.0227.

Provenance & Evidence