反应详情

To a solution of 5-(1-piperazinyl)-quinoline (500 mg, 2.35 mmol), 4-(5-cyano-1H-3-indolyl)-cyclohexanone (540 mg, 2.35 mmol), and sodium triacetoxyborohydride (740 mg, 3.5 mmol) in dichloroethane (20 mL) was added acetic acid (0.27 mL, 4.7 mmol) and stirred overnight at room temperature. The reaction was quenched with 1 M NaOH (50 mL) and extracted in CH2Cl2 (3×100 mL). The organic fractions were combined, dried over Na2SO4, concentrated, filtered and chromatographed (5% MeOH/EtOAc) yielding 410 mg (41%) of the cis isomer as a white solid. The HCl salt was generated from EtOAc yielding a white solid: mp 220-223° C.

1. customThe reaction was quenched with 1 M NaOH (50 mL)
2. extractionextracted in CH2Cl2 (3×100 mL)
3. dry with materialdried over Na2SO4
4. concentrationconcentrated
5. filtrationfiltered
6. customchromatographed (5% MeOH/EtOAc)
7. customyielding 410 mg (41%) of the cis isomer as a white solid