反应详情

Under ice cooling, sodium hydride (60% oil, 141 mg) was added to a DMF (20 ml) solution of (3-cyanobenzyl)(triphenyl)phosphonium bromide (1.6 g) and tert-butyl 4-formyl-1-piperidinecarboxylate (0.75 g), followed by stirring overnight at room temperature. The reaction liquid was diluted with EtOAc, washed with water, and dried over anhydrous magnesium sulfate. The solvent was evaporated, and the resulting residue was purified by silica gel column chromatography (eluent: hexane:EtOAc=6:1 (v/v)) to obtain an oil. 10% Palladium-carbon (100 mg) was added to an EtOAc (30 ml) solution of the resulting oil, followed by stirring in a hydrogen stream atmosphere for 2 hours. The catalyst was removed with Celite, and the solvent was concentrated to obtain an oil. The resulting oil was dissolved in EtOAc (10 ml), and 4 M hydrogen chloride/EtOAc solution (5 ml) was added thereto, then stirred at room temperature for 6 hours, and then concentrated. The resulting solid was washed with ether and dried under reduced pressure to obtain 3-[2-(4-piperidinyl)ethyl]benzonitrile hydrochloride (506 mg).

1. customThe reaction liquid
2. washwashed with water
3. dry with materialdried over anhydrous magnesium sulfate
4. customThe solvent was evaporated
5. customthe resulting residue was purified by silica gel column chromatography (eluent: hexane:EtOAc=6:1 (v/v))
6. customto obtain an oil
7. customThe catalyst was removed with Celite
8. concentrationthe solvent was concentrated
9. customto obtain an oil
10. stirringstirred at room temperature for 6 hours
11. concentrationconcentrated
12. washThe resulting solid was washed with ether
13. customdried under reduced pressure