反应详情

To a solution of 1-(2-chloro-4-nitrobenzyl)-4-methylpiperazine (0.96 g, 3.6 mmol) in MeOH/water (4:1, 50 mL) was added 1.80 g (33.7 mmol) of NH4Cl and 1.47 g (26.3 mmol) of Fe dust and the mixture heated at reflux under an atmosphere of N2 for 2 h (HPLC indicated no progress). To this was added 4 mL of glacial acetic acid and the mixture heated at reflux for an additional 2 h. The reaction mixture was cooled to ambient temperature, filtered, and the filtrate concentrated. The residue was partitioned between EtOAc and saturated aq. NaHCO3, the separated aqueous layer was extracted with EtOAc, and the combined organics washed with brine and dried over Na2SO4. Upon concentration, the crude product was purified by silica gel chromatography (eluted with 5-7% MeOH/DCM; silica gel deactivated with 1% triethylamine/DCM) to provide 0.53 g of product.

1. temperaturethe mixture heated
2. temperatureat reflux under an atmosphere of N2 for 2 h (HPLC
3. temperaturethe mixture heated
4. temperatureat reflux for an additional 2 h
5. filtrationfiltered
6. concentrationthe filtrate concentrated
7. customThe residue was partitioned between EtOAc and saturated aq. NaHCO3
8. extractionthe separated aqueous layer was extracted with EtOAc
9. washthe combined organics washed with brine
10. dry with materialdried over Na2SO4
11. concentrationUpon concentration
12. customthe crude product was purified by silica gel chromatography (eluted with 5-7% MeOH/DCM; silica gel deactivated with 1% triethylamine/DCM)