Triethylamine → HCID 13768044, compound

HRID 1789357Notes

Reaction equation

HRID 1789357 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[O:16][CH2:17][CH2:18][N:19]1[CH2:24][CH2:23][N:22]([C:25]2[CH:30]=[CH:29][CH:28]=[C:27]([F:31])[CH:26]=2)[CH2:21][CH2:20]1)=[O:4].[C:32](Cl)(=[O:35])[CH2:33][CH3:34].C(N(CC)CC)C>C1(C)C=CC=CC=1>[CH3:1][N:2]([C:32](=[O:35])[CH2:33][CH3:34])[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][CH2:17][CH2:18][N:19]1[CH2:24][CH2:23][N:22]([C:25]2[CH:30]=[CH:29][CH:28]=[C:27]([F:31])[CH:26]=2)[CH2:21][CH2:20]1)=[O:4]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 62324Propionyl chlorideHCID 13767930HCID 13767930, compound

Product 1

HCID 13768044HCID 13768044, compoundYield 12%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 2.22 g of N-methyl-2-{2-[2-(4-(3-fluorophenyl)piperazin-1-yl)ethyloxy]phenyl}thiazolidine-3-carboxamide, 1.39 g of propionyl chloride, 2.53 g of triethylamine and 50 ml of toluene is refluxed for 2.5 days with stirring. 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 a saturated sodium bicarbonate solution and a saturated sodium chloride solution, successively. The ethyl acetate solution is dried and then concentrated under reduced pressure to remove solvent. The residue is purified by silica gel chromatography (solvent, chloroform:ethyl acetate=3:1). 0.30 g of N-methyl-N-propionyl-2-{2-[2-(4-(3-fluorophenyl)piperazine-1-yl)ethyloxy]phenyl}thiazolidine-3-carboxamide is obtained as an oil.

Workup

  1. temperatureis refluxed for 2.5 days
  2. concentrationThe mixture is concentrated under reduced pressure
  3. customto remove solvent
  4. additionWater is added to the residue
  5. extractionthe aqueous mixture is extracted with ethyl acetate
  6. washThe extract is washed with a saturated sodium bicarbonate solution
  7. dry with materialThe ethyl acetate solution is dried
  8. concentrationconcentrated under reduced pressure
  9. customto remove solvent
  10. customThe residue is purified by silica gel chromatography (solvent, chloroform:ethyl acetate=3:1)

Sources & evidence

ORD record
ord-32f84dbb0b9d4ce7a27403d9bb0ba450
Source dataset
uspto-grants-1987_08
Patent number
US04689327

Reaction notes

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