Sodium Iodide → N-methyl-2-{2-[2-(4-phenylpiperazin-1-yl)ethyloxy]phenyl}thiazolidine-3-carboxamide

HRID 1789347Notes

Reaction equation

HRID 1789347 reaction equation
[CH3:1][NH:2][C:3]([N:5]1[CH2:9][CH2:8][S:7][CH:6]1[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[OH:16])=[O:4].C(=O)([O-])[O-].[K+].[K+].[I-].[Na+].Cl[CH2:26][CH2:27][N:28]1[CH2:33][CH2:32][N:31]([C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[CH2:30][CH2:29]1>CN(C)C=O>[CH3:1][NH:2][C:3]([N:5]1[CH2:9][CH2:8][S:7][CH:6]1[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[O:16][CH2:26][CH2:27][N:28]1[CH2:33][CH2:32][N:31]([C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[CH2:30][CH2:29]1)=[O:4]

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 47418781-(2-Chloroethyl)-4-phenylpiperazineHCID 137496082-(2-Hydroxyphenyl)-N-methyl-1,3-thiazolidine-3-carboxamide

Product 1

HCID 13767927N-methyl-2-{2-[2-(4-phenylpiperazin-1-yl)ethyloxy]phenyl}thiazolidine-3-carboxamideYield 44.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of 2.38 g of N-methyl-2-(2-hydroxyphenyl)thiazolidine-3-carboxamide, 1.38 g of potassium carbonate, 0.7 g of sodium iodide, 3.36 g of 1-(2-chloroethyl)-4-phenylpiperazine and 25 ml of dimethylformamide is stirred at 90° C. for 24 hours. The mixture is concentrated under reduced pressure to remove dimethylformamide. Water is added to the residue, and the aqueous mixture is extacted with ethyl acetate. The extract is washed with dilute sodium hydroxide solution and water, successively. The ethyl acetate solution is dried and then concentrated under reduced pressure to remove solvent. The residue is purified by silica gel chromatography (sovent, benzene:ethyl acetate-1:5). 1.89 g of N-methyl-2-{2-[2-(4-phenylpiperazin-1-yl)ethyloxy]phenyl}thiazolidine-3-carboxamide are obtained.

Workup

  1. concentrationThe mixture is concentrated under reduced pressure
  2. customto remove dimethylformamide
  3. additionWater is added to the residue
  4. washThe extract is washed with dilute sodium hydroxide solution and water
  5. dry with materialThe ethyl acetate solution is dried
  6. concentrationconcentrated under reduced pressure
  7. customto remove solvent
  8. customThe residue is purified by silica gel chromatography (sovent, benzene:ethyl acetate-1:5)

Sources & evidence

ORD record
ord-99a2331c88664704a50a163db33a54cd
Source dataset
uspto-grants-1987_08
Patent number
US04689327

Reaction notes

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