Benzocaine → Ethyl 4-(piperazin-1-yl)benzoate

HRID 655604Notes

Reaction equation

HRID 655604 reaction equation
Cl.Cl[CH2:3][CH2:4][NH:5][CH2:6][CH2:7]Cl.[CH2:9]([O:11][C:12](=[O:20])[C:13]1[CH:18]=[CH:17][C:16]([NH2:19])=[CH:15][CH:14]=1)[CH3:10].C(=O)([O-])[O-].[K+].[K+]>ClC1C=CC=CC=1>[CH2:9]([O:11][C:12](=[O:20])[C:13]1[CH:18]=[CH:17][C:16]([N:19]2[CH2:7][CH2:6][NH:5][CH2:4][CH2:3]2)=[CH:15][CH:14]=1)[CH3:10]

Participants

5

Reactant 3

HCID 2337BenzocaineHCID 11430Potassium CarbonateHCID 522769Bis(2-chloroethyl)amine hydrochloride

Product 1

HCID 2761178Ethyl 4-(piperazin-1-yl)benzoateYield 73%

Reagents, catalysts & solvents 1

HCID 7964ChlorobenzeneSolvent

Procedure

A stirred mixture of bis-(2-chloroethyl)amine hydrochloride (5.35 g, 30.00 mmol), 4-aminobenzoic acid ethyl ester (4.13 g, 25.00 mmol), and potassium carbonate (4.40 g, 32.00 mmol) in chlorobenzene (200 mL) was refluxed for 30 hours. After cooling to ambient temperature the mixture was filtered and the filtrate was concentrated in vacuo to dryness to provide 4.27 g (73% yield) of 4-piperazin-1-yl-benzoic acid ethyl ester.

Workup

  1. temperaturewas refluxed for 30 hours
  2. filtrationwas filtered
  3. concentrationthe filtrate was concentrated in vacuo to dryness

Sources & evidence

ORD record
ord-1f930b046ee34995affcdae08c368724
Source dataset
uspto-grants-2011_12
Patent number
US08071603B2

Reaction notes

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