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

HRID 1250536Notes

Reaction equation

HRID 1250536 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-3e01fad2c9aa4c28bdd58d6baf0ac502
Source dataset
uspto-grants-2002_01
Patent number
US06339087B1

Reaction notes

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