Dimethylacetamide → Ethyl 4-(4-benzylpiperazin-1-yl)benzoate

HRID 359402Notes

Reaction equation

HRID 359402 reaction equation
[C:1]1([CH2:7][N:8]2[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.F[C:15]1[CH:25]=[CH:24][C:18]([C:19]([O:21][CH2:22][CH3:23])=[O:20])=[CH:17][CH:16]=1.CN(C)C(=O)C>O>[C:1]1([CH2:7][N:8]2[CH2:9][CH2:10][N:11]([C:15]3[CH:25]=[CH:24][C:18]([C:19]([O:21][CH2:22][CH3:23])=[O:20])=[CH:17][CH:16]=3)[CH2:12][CH2:13]2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 31374DimethylacetamideHCID 67976Benzoic acid, 4-fluoro-, ethyl esterHCID 759941-Benzylpiperazine

Product 1

HCID 14765277Ethyl 4-(4-benzylpiperazin-1-yl)benzoateYield 77%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 17.6 parts of 1-(phenylmethyl)piperazine, 8.4 parts of ethyl 4-fluorobenzoate and 45 parts of N,N-dimethylacetamide was stirred and refluxed for 22 hours. The reaction mixture was cooled and poured onto 500 parts of water. The product was extracted three times with benzene. The combined extracts were washed three times with a lot of water, dried, filtered and evaporated. The residue was stirred in hexane. The product was filtered off, washed with hexane and dried in vacuo, yielding 12.5 parts (77%) of ethyl 4-[4-(phenylmethyl)-1-piperazinyl]benzoate (intermediate 2).

Workup

  1. temperaturerefluxed for 22 hours
  2. temperatureThe reaction mixture was cooled
  3. extractionThe product was extracted three times with benzene
  4. washThe combined extracts were washed three times with a lot of water
  5. customdried
  6. filtrationfiltered
  7. customevaporated
  8. stirringThe residue was stirred in hexane
  9. filtrationThe product was filtered off
  10. washwashed with hexane
  11. customdried in vacuo

Sources & evidence

ORD record
ord-e222a38f39644b549b771e44ab9436cf
Source dataset
uspto-grants-1991_03
Patent number
US05001125

Reaction notes

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