1-Piperazinecarboxylic acid, ethyl ester → 113240-38-3

HRID 1381874Notes

Reaction equation

HRID 1381874 reaction equation
[OH-].[K+].C(OC([N:8]1[CH2:13][CH2:12][N:11]([CH2:14][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([Cl:22])[CH:17]=2)[CH2:10][CH2:9]1)=O)C.C(OC(N1CCNCC1)=O)C.ClC1C=C(CCBr)C=CC=1>O.C1(C)C=CC=CC=1.C(O)C>[Cl:22][C:18]1[CH:17]=[C:16]([CH2:15][CH2:14][N:11]2[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]2)[CH:21]=[CH:20][CH:19]=1

Participants

8

Reactant 4

HCID 84311-Piperazinecarboxylic acid, ethyl esterHCID 14797Potassium HydroxideHCID 1401401-(2-Bromoethyl)-3-chlorobenzeneHCID 21275352Ethyl 4-[2-(3-chlorophenyl)ethyl]-1-piperazinecarboxylate

Product 1

HCID 19007104113240-38-3

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolvent2×HCID 1140TolueneSolvent

Procedure

50 ml of ethanol, 50 g of potassium hydroxide and 8.8 ml of water are added to 39.8 g of 1-ethoxycarbonyl-4-[2-(3-chlorophenyl)-ethyl]-piperazine, obtainable by reacting 17.7 g of 1-ethoxycarbonylpiperazine and 24.6 g of 2-(3-chlorophenyl)-ethyl bromide while heating at 120°-125° under nitrogen, and the whole is heated under reflux for 3 hours. The whole is then allowed to cool, is diluted with 300 ml of water and 300 ml of toluene and shaken thoroughly, and then the organic phase is separated off, washed with saturated sodium chloride solution, dried over sodium sulphate and concentrated to dryness by evaporation under reduced pressure. 1-[2-(3-chlorophenyl)-ethyl]piperazine is obtained and can be purified via the hydrochloride (m.p. 260°) from which it can then be freed again by treatment with sodium hydroxide solution, separation with diethyl ether and evaporation of the latter.

Workup

  1. temperaturewhile heating at 120°-125° under nitrogen
  2. temperaturethe whole is heated
  3. temperatureunder reflux for 3 hours
  4. temperatureto cool
  5. customthe organic phase is separated off
  6. washwashed with saturated sodium chloride solution
  7. dry with materialdried over sodium sulphate
  8. concentrationconcentrated to dryness by evaporation under reduced pressure

Sources & evidence

ORD record
ord-581410a684fd4e209b4c71ada74e4c5a
Source dataset
uspto-grants-1989_02
Patent number
US04804661

Reaction notes

Loading…