Ethanol → Ethyl [1-(3,4-dichlorobenzyl)piperidin-4-yl]acetate

HRID 1610907Notes

Reaction equation

HRID 1610907 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:18]=[CH:19][C:20]=1[Cl:21])[CH2:5][N:6]1[CH2:11][CH2:10][C:9](=[CH:12][C:13]([O:15][CH2:16][CH3:17])=[O:14])[CH2:8][CH2:7]1.C(O)C>O1CCCC1.[Pt]=O>[Cl:1][C:2]1[CH:3]=[C:4]([CH:18]=[CH:19][C:20]=1[Cl:21])[CH2:5][N:6]1[CH2:7][CH2:8][CH:9]([CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14])[CH2:10][CH2:11]1

Participants

5

Reactant 2

HCID 702EthanolHCID 18351421HCID 18351421, compound

Product 1

HCID 10758769Ethyl [1-(3,4-dichlorobenzyl)piperidin-4-yl]acetateYield 99.5%

Reagents, catalysts & solvents 2

HCID 82844Platinum oxide (PtO)CatalystHCID 8028TetrahydrofuranSolvent

Procedure

Ethyl [1-(3,4-dichlorobenzyl)piperidin-4-ylidene]acetate (3.9 g, 11.9 mmol) dissolved in tetrahydrofuran (25 ml) and ethanol (25 ml) was subjected to hydrogenation over platinum oxide (0.1 g) at ambient temperature and atmospheric pressure. The reaction mixture was filtered through a celite pad and concentrated in vacuo to give ethyl [1-(3,4-dichlorobenzyl)piperidin-4-yl]acetate (3.91 g) as a semi-solid.

Workup

  1. filtrationThe reaction mixture was filtered through a celite pad
  2. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-d6a9b6a674a246d599c57c0f981895dd
Source dataset
uspto-grants-2006_01
Patent number
US06984637B2

Reaction notes

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