4-(1-Benzyl-1,2,5,6-tetrahydropyrid-4-yl)phenethyl alcohol → 2-(4-(Piperidin-4-YL)phenyl)ethanol
Reaction equation
C([N:8]1[CH2:13][CH2:12][C:11]([C:14]2[CH:22]=[CH:21][C:17]([CH2:18][CH2:19][OH:20])=[CH:16][CH:15]=2)=[CH:10][CH2:9]1)C1C=CC=CC=1>C(O)C.[C].[Pd]>[NH:8]1[CH2:13][CH2:12][CH:11]([C:14]2[CH:22]=[CH:21][C:17]([CH2:18][CH2:19][OH:20])=[CH:16][CH:15]=2)[CH2:10][CH2:9]1Participants
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Procedure
To a solution of 8.0 g of 4-(1-benzyl-1,2,5,6-tetrahydropyrid-4-yl)phenethyl alcohol in ethanol (200 ml) was added 15 g of 10% palladium-carbon (moisture content: 50%) and hydrogenation was effected at ordinary temperature under atmospheric pressure for 12 hours. After the completion of the reaction, the palladium-carbon was filtered off and the filtrate was distilled under reduced pressure to thereby give 4.0 g of crude 4-(piperidin-4-yl)phenethyl alcohol as a colorless oily substance. To 4.0 g of this crude product and 3.3 ml of triethylamine dissolved in dichloromethane (30 ml) was added 3.1 ml of benzyl chloroformate at 0° C. and the mixture was reacted at room temperature for 1 hour. After adding water, the reaction mixture was extracted with ethyl acetate, washed with a saturated aqueous solution of sodium chloride and dried over anhydrous magnesium sulfate. After distilling off the solvent under reduced pressure, the residue was purified by silica gel column chromatography (eluted with n-hexane/ethyl acetate) to thereby give 4.0 g of the title compound as a yellow oily substance.
Workup
- customAfter the completion of the reaction
- filtrationthe palladium-carbon was filtered off
- distillationthe filtrate was distilled under reduced pressure
Sources & evidence
- ORD record
- ord-8921c57019f04545b62827e1269cd8ee
- Source dataset
- uspto-grants-2003_02
- Patent number
- US06518423B1
Reaction notes
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