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

HRID 1840753Notes

Reaction equation

HRID 1840753 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-b2c98065bcf94f6bb8a5fb7df4a7f280
Source dataset
uspto-grants-2004_01
Patent number
US06683074B1

Reaction notes

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