1-(3-Chlorophenyl)piperazine → 1-Piperazineacetic acid, 4-(3-chlorophenyl)-α-methyl-, ethyl ester

HRID 986207Notes

Reaction equation

HRID 986207 reaction equation
[C:1]([O:5][CH2:6][CH3:7])(=[O:4])[CH:2]=[CH2:3].[Cl:8][C:9]1[CH:10]=[C:11]([N:15]2[CH2:20][CH2:19][NH:18][CH2:17][CH2:16]2)[CH:12]=[CH:13][CH:14]=1>C(O)C>[CH2:6]([O:5][C:1](=[O:4])[CH:2]([N:18]1[CH2:17][CH2:16][N:15]([C:11]2[CH:12]=[CH:13][CH:14]=[C:9]([Cl:8])[CH:10]=2)[CH2:20][CH2:19]1)[CH3:3])[CH3:7]

Participants

4

Reactant 2

HCID 13551-(3-Chlorophenyl)piperazineHCID 8821Ethyl Acrylate

Product 1

HCID 617213111-Piperazineacetic acid, 4-(3-chlorophenyl)-α-methyl-, ethyl ester

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Over a period of 40 minutes, 108 ml of ethyl acrylate are added to 38.3 g of N-(3-chlorophenyl)piperazine dissolved in 300 ml of anhydrous ethanol and 0.5 ml of Triton B. The temperature reaches 40° C. when addition is complete. After heating at reflux for 3 hours, the reaction mixture is concentrated in vacuo and the residue is distilled. 139 g of 4-(3-chlorophenyl)piperazin-1-ylpropionic acid ethyl ester are obtained, b.p/0.33 mmHg=176°-179° C.

Workup

  1. customreaches 40° C.
  2. additionwhen addition
  3. temperatureAfter heating
  4. temperatureat reflux for 3 hours
  5. concentrationthe reaction mixture is concentrated in vacuo
  6. distillationthe residue is distilled

Sources & evidence

ORD record
ord-245179c9bc514222afcc1bbbd1aa7586
Source dataset
uspto-grants-1987_12
Patent number
US04711885

Reaction notes

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