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

HRID 1835262Notes

Reaction equation

HRID 1835262 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-0bc48382223240fba5c95595b89c8242
Source dataset
uspto-grants-2004_08
Patent number
US06770650B2

Reaction notes

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