反应详情

A 250-mL round-bottomed flask was charged with N-(((2S)-1,4-dibenzyl-2-piperazinyl)methyl)aniline (0.734 g, 1.98 mmol), DMAP (0.027 g, 0.22 mmol), triethylamine (0.85 mL, 6.1 mmol) and CH2Cl2 (8 mL). Methanesulfonyl chloride (0.23 mL, 3.0 mmol) was added drop wise at room temperature and the mixture was stirred at room temperature for 2 h. Additional methanesulfonyl chloride (0.20 mL, 2.6 mmol) and triethylamine (1.0 mL, 7.2 mmol) were added. The mixture was stirred at room temperature for another 1.5 h and then the mixture was concentrated to half the original volume and partitioned between water (40 mL) and EtOAc (40 mL). The aqueous phase was extracted with EtOAc (30 mL). The combined organic phases were washed with saturated aqueous NaCl (50 mL), dried over sodium sulfate, filtered and concentrated in vacuo. The crude product was purified by column chromatography (25 g of silica gel, 0 to 60% EtOAc in hexanes) to afford N-(((2R)-1,4-dibenzyl-2-piperazinyl)methyl)-N-phenylmethanesulfonamide (0.528 g) as a light yellow solid.

1. stirringThe mixture was stirred at room temperature for another 1.5 h
2. concentrationthe mixture was concentrated to half the original volume
3. custompartitioned between water (40 mL) and EtOAc (40 mL)
4. extractionThe aqueous phase was extracted with EtOAc (30 mL)
5. washThe combined organic phases were washed with saturated aqueous NaCl (50 mL)
6. dry with materialdried over sodium sulfate
7. filtrationfiltered
8. concentrationconcentrated in vacuo
9. customThe crude product was purified by column chromatography (25 g of silica gel, 0 to 60% EtOAc in hexanes)