Acetyl chloride → N-acetyl-N-methyl-2-{2-[2-(4-(3-fluorophenyl)piperazin-1-yl)ethyloxy]phenyl}thiazolidine-3-carboxamide

HRID 1789356Notes

Reaction equation

HRID 1789356 reaction equation
[H-].[Na+].[CH3:3][NH:4][C:5]([N:7]1[CH2:11][CH2:10][S:9][CH:8]1[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[O:18][CH2:19][CH2:20][N:21]1[CH2:26][CH2:25][N:24]([C:27]2[CH:32]=[CH:31][CH:30]=[C:29]([F:33])[CH:28]=2)[CH2:23][CH2:22]1)=[O:6].[C:34](Cl)(=[O:36])[CH3:35]>CN(C)C=O.CCOCC>[C:34]([N:4]([CH3:3])[C:5]([N:7]1[CH2:11][CH2:10][S:9][CH:8]1[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[O:18][CH2:19][CH2:20][N:21]1[CH2:22][CH2:23][N:24]([C:27]2[CH:32]=[CH:31][CH:30]=[C:29]([F:33])[CH:28]=2)[CH2:25][CH2:26]1)=[O:6])(=[O:36])[CH3:35]

Participants

6

Reactant 3

HCID 6367Acetyl chlorideHCID 24758Sodium hydrideHCID 13767930HCID 13767930, compound

Product 1

HCID 13768041N-acetyl-N-methyl-2-{2-[2-(4-(3-fluorophenyl)piperazin-1-yl)ethyloxy]phenyl}thiazolidine-3-carboxamide

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

0.1 g of sodium hydride (60% oil dispersion) is added to a solution of one g of N-methyl-2-{2-[2-(4-(3-fluorophenyl)piperazin-1-yl)ethyloxy]phenyl}thiazolidine-3-carboxamide in 30 ml of dimethylformamide, and a solution of 0.19 g of acetyl chloride in 5 ml of ether is added thereto. After the mixture is stirred at 50° C. for 20 hours, the mixture is concentrated under reduced pressure to remove solvent. Water is added to the residue, and the aqueous mixture is extracted with ethyl acetate. 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, ethyl acetate:n-hexane=4:1). 0.32 g of N-acetyl-N-methyl-2-{2-[2-(4-(3-fluorophenyl)piperazin-1-yl)ethyloxy]phenyl}thiazolidine-3-carboxamide is obtained as an oil.

Workup

  1. concentrationthe mixture is concentrated under reduced pressure
  2. customto remove solvent
  3. additionWater is added to the residue
  4. extractionthe aqueous mixture is extracted with ethyl acetate
  5. washThe extract is washed with water
  6. customdried
  7. concentrationconcentrated under reduced pressure
  8. customto remove solvent
  9. customThe residue is purified by silica gel chromatography (solvent, ethyl acetate:n-hexane=4:1)

Sources & evidence

ORD record
ord-cc5689b69bf7423889aa61414394c6d6
Source dataset
uspto-grants-1987_08
Patent number
US04689327

Reaction notes

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