1-Phenylpiperazine → 1-(4-Phenyl-2-thiazolylmethyl)-4-phenylpiperazine

HRID 1112731Notes

Reaction equation

HRID 1112731 reaction equation
Cl[CH2:2][C:3]1[S:4][CH:5]=[C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[N:7]=1.[C:14]1([N:20]2[CH2:25][CH2:24][NH:23][CH2:22][CH2:21]2)[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.C(=O)([O-])[O-].[Na+].[Na+]>C(O)C>[C:8]1([C:6]2[N:7]=[C:3]([CH2:2][N:23]3[CH2:24][CH2:25][N:20]([C:14]4[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=4)[CH2:21][CH2:22]3)[S:4][CH:5]=2)[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

5

Reactant 3

HCID 70961-PhenylpiperazineHCID 10340Sodium CarbonateHCID 225573612-(Chloromethyl)-4-phenyl-1,3-thiazole

Product 1

HCID 227625081-(4-Phenyl-2-thiazolylmethyl)-4-phenylpiperazineYield 75%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of crude 2-chloromethyl-4-phenylthiazole (4.19g; 0.02 mole), N-phenylpiperazine (3.24 g; 0.02 mole) and finely-powdered, anhydrous sodium carbonate in absolute ethanol (60 ml) was stirred and boiled under reflux for 8 hours. The solvent was evaporated to dryness, solid residue suspended in water (100 ml) and then extracted with 2 × 100 ml CH2Cl2. The extracts were washed with water and dried over anhydrous MgSO4. On evaporation of the solvent, and recrystallisation of the residue from benzene/60°-80° C. petroleum ether mixture (with charcoal treatment) there was obtained the required product (5.03 g; 75%) having m.p. 142°-3° C.

Workup

  1. temperatureunder reflux for 8 hours
  2. customThe solvent was evaporated to dryness, solid residue
  3. extractionextracted with 2 × 100 ml CH2Cl2
  4. washThe extracts were washed with water
  5. dry with materialdried over anhydrous MgSO4
  6. customOn evaporation of the solvent, and recrystallisation of the residue from benzene/60°-80° C. petroleum ether mixture (with charcoal treatment) there

Sources & evidence

ORD record
ord-163721578a66400cba94f5152a80b4bd
Source dataset
uspto-grants-1978_10
Patent number
US04123529

Reaction notes

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