Sodium benzenethiolate → 1-[2-(4-Chlorophenyl)ethyl]piperazine

HRID 1975358Notes

Reaction equation

HRID 1975358 reaction equation
C(O)(=O)/C=C/C(O)=O.C(OCCN(C1C=CC(C([N:26]2[CH2:31][CH2:30][N:29]([CH2:32][CH2:33][C:34]3[CH:39]=[CH:38][C:37]([Cl:40])=[CH:36][CH:35]=3)[CH2:28][CH2:27]2)=O)=CC=1)C(=O)CCl)(C)C.C1([S-])C=CC=CC=1.[Na+]>C(O)C>[Cl:40][C:37]1[CH:38]=[CH:39][C:34]([CH2:33][CH2:32][N:29]2[CH2:28][CH2:27][NH:26][CH2:31][CH2:30]2)=[CH:35][CH:36]=1

Participants

4

Reactant 2

HCID 4110039Sodium benzenethiolate2×HCID 190994641-{4-[N-(2-isopropyloxyethyl)-N-chloroacetylamino]benzoyl}-4-[2-(4-chlorophenyl)ethyl]piperazine fumarate

Product 1

HCID 122357141-[2-(4-Chlorophenyl)ethyl]piperazine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

5 g of 1-{4-[N-(2-isopropyloxyethyl)-N-chloroacetylamino]benzoyl}-4-[2-(4-chlorophenyl)ethyl]piperazine (Example 3) are dissolved in 50 ml of absolute ethanol, and 1.471 g of sodium thiophenolate are added. The mixture is stirred for one hour at room temperature and a further 1 g of sodium thiophenolate is added. The mixture is stirred for a further 3 hours at RT and then the reaction solution is concentrated by evaporation. The oily residue is extracted with ether and the ethereal phases are washed in succession with water, soda solution and water a concentrated by evaporation, and the light-yellow oil is crystallised from ether and hexane, yielding 1-{4-[N-(2-isopropyloxyethyl)-N-phenylmercaptoacetylamino]benzoyl{-4-[2-(4-chlorophenyl)ethyl]piperazine having a melting point of 47°-49°.

Workup

  1. stirringThe mixture is stirred for a further 3 hours at RT
  2. concentrationthe reaction solution is concentrated by evaporation
  3. extractionThe oily residue is extracted with ether
  4. washthe ethereal phases are washed in succession with water, soda solution and water
  5. concentrationa concentrated by evaporation
  6. customthe light-yellow oil is crystallised from ether and hexane

Sources & evidence

ORD record
ord-e6dcf6ae5a2e4e4e96b73f56a1d57f61
Source dataset
uspto-grants-1994_02
Patent number
US05286728

Reaction notes

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