Piperazine → 3-Fluoro4-piperazin-1-yl-benzoic acid ethyl ester

HRID 736123Notes

Reaction equation

HRID 736123 reaction equation
[CH2:1]([O:3][C:4](=[O:13])[C:5]1[CH:10]=[CH:9][C:8](F)=[C:7]([F:12])[CH:6]=1)[CH3:2].[NH:14]1[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]1>CN(C)C(=O)C>[CH2:1]([O:3][C:4](=[O:13])[C:5]1[CH:10]=[CH:9][C:8]([N:14]2[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]2)=[C:7]([F:12])[CH:6]=1)[CH3:2]

Participants

4

Reactant 2

HCID 4837PiperazineHCID 2737171Ethyl 3,4-difluorobenzoate

Product 1

HCID 207856163-Fluoro4-piperazin-1-yl-benzoic acid ethyl esterYield 91%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of 5 g (27 mmol) 3,4-Difluoro-benzoic acid ethyl ester and 11.56 g (134 mmol) piperazine in 15 ml N,N-dimethylacetamide was heated to 120° C. for 1.5 h and subsequently all volatiles were removed under vacuum. The residue was purified by flash column chromatography on silica eluting with DCM/methanol to yield 6.19 g (91%) of the title compound as white amorphous solid.

Workup

  1. customsubsequently all volatiles were removed under vacuum
  2. customThe residue was purified by flash column chromatography on silica eluting with DCM/methanol

Sources & evidence

ORD record
ord-d7fae6fd54b6434a871830e431eedfd9
Source dataset
uspto-grants-2009_09
Patent number
US07595314B2

Reaction notes

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