Piperine → Tetrahydropiperine

HRID 1699365Notes

Reaction equation

HRID 1699365 reaction equation
[CH:1]1[C:6](/[CH:7]=[CH:8]/[CH:9]=[CH:10]/[C:11]([N:13]2[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]2)=[O:12])=[CH:5][C:4]2[O:19][CH2:20][O:21][C:3]=2[CH:2]=1.[H][H]>C(O)C.[Pd]>[CH:1]1[C:6]([CH2:7][CH2:8][CH2:9][CH2:10][C:11]([N:13]2[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18]2)=[O:12])=[CH:5][C:4]2[O:19][CH2:20][O:21][C:3]=2[CH:2]=1

Participants

5

Reactant 2

HCID 638024PiperineHCID 178418361HCID 178418361, compound

Product 1

HCID 581676TetrahydropiperineYield 78.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

Piperine (2 g, 7 mmol) was hydrogenated in ethanol (50 ml) over 5% Pd-C under a pressure of hydrogen at 10 psi for 30 mins to give tetrahydropiperine (1.59 g, 78% yield) as an oil2.

Sources & evidence

ORD record
ord-343219fe52b54a44b6e589b4e37ca5be
Source dataset
uspto-grants-2002_02
Patent number
US06346539B1

Reaction notes

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