Water → N-ethoxycarbonyl-2-{2-[2-(4-(3-fluorophenyl)piperazin-1-yl)ethyloxy]phenyl}thiazolidine-3-carboxamide

HRID 1789353Notes

Reaction equation

HRID 1789353 reaction equation
[CH2:1]([O:3][C:4]([N:6]=[C:7]=[O:8])=[O:5])[CH3:2].[F:9][C:10]1[CH:11]=[C:12]([N:16]2[CH2:21][CH2:20][N:19]([CH2:22][CH2:23][O:24][C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=3[CH:31]3[NH:35][CH2:34][CH2:33][S:32]3)[CH2:18][CH2:17]2)[CH:13]=[CH:14][CH:15]=1.O.C(=O)([O-])[O-].[K+].[K+]>O1CCCC1>[CH2:1]([O:3][C:4]([NH:6][C:7]([N:35]1[CH2:34][CH2:33][S:32][CH:31]1[C:26]1[CH:27]=[CH:28][CH:29]=[CH:30][C:25]=1[O:24][CH2:23][CH2:22][N:19]1[CH2:18][CH2:17][N:16]([C:12]2[CH:13]=[CH:14][CH:15]=[C:10]([F:9])[CH:11]=2)[CH2:21][CH2:20]1)=[O:8])=[O:5])[CH3:2]

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 300166ethyl N-carbonylcarbamate2×HCID 13768101HCID 13768101, compound

Product 1

HCID 13768038N-ethoxycarbonyl-2-{2-[2-(4-(3-fluorophenyl)piperazin-1-yl)ethyloxy]phenyl}thiazolidine-3-carboxamideYield 40.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

0.9 g of ethoxycarbonyl isocyanate is added to a solution of 2 g of 2-{2-[2-(4-(3-fluorophenyl)piperazin-1-yl)ethyloxy]phenyl}thiazolidine in 30 ml of tetrahydrofuran, and the mixture is stirred at room temperature for 18 hours. 3.1 g of ethoxycarbonyl isocyanate are added to the mixture, and the mixture is stirred at room temperature for 2 hours. Water is added to the mixture, and the aqueous mixture is made alkaline with potassium carbonate. The aqueous mixture is extracted with ethyl acetate, and the extract is washed with water, dried and then concentrated under reduced pressure to remove solvent. The residue is purified by silica gel chromatography (solvent, benzene:ethyl acetate=1:1). 1.05 g of N-ethoxycarbonyl-2-{2-[2-(4-(3-fluorophenyl)piperazin-1-yl)ethyloxy]phenyl}thiazolidine-3-carboxamide are obtained as an amorphous powder.

Workup

  1. stirringthe mixture is stirred at room temperature for 2 hours
  2. extractionThe aqueous mixture is extracted with ethyl acetate
  3. washthe extract is washed with water
  4. customdried
  5. concentrationconcentrated under reduced pressure
  6. customto remove solvent
  7. customThe residue is purified by silica gel chromatography (solvent, benzene:ethyl acetate=1:1)

Sources & evidence

ORD record
ord-eaa3856354d9479ba50679c11149fbdb
Source dataset
uspto-grants-1987_08
Patent number
US04689327

Reaction notes

Loading…