Dimethylformamide → 4-[4-(3-Indolyl)piperidinomethyl]-2-(2-acetoxyacetylamino)thiazole

HRID 1252075Notes

Reaction equation

HRID 1252075 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([CH:10]2[CH2:15][CH2:14][N:13]([CH2:16][C:17]3[N:18]=[C:19]([NH2:22])[S:20][CH:21]=3)[CH2:12][CH2:11]2)=[CH:2]1.C(N(CC)CC)C.CN(C)C=O.[C:35]([O:38][CH2:39][C:40](Cl)=[O:41])(=[O:37])[CH3:36]>C(Cl)Cl>[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([CH:10]2[CH2:15][CH2:14][N:13]([CH2:16][C:17]3[N:18]=[C:19]([NH:22][C:40](=[O:41])[CH2:39][O:38][C:35](=[O:37])[CH3:36])[S:20][CH:21]=3)[CH2:12][CH2:11]2)=[CH:2]1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 8471TriethylamineHCID 26297Acetoxyacetyl chlorideHCID 141297964-((4-(1H-Indol-3-yl)piperidin-1-yl)methyl)thiazol-2-amine

Product 1

HCID 141297994-[4-(3-Indolyl)piperidinomethyl]-2-(2-acetoxyacetylamino)thiazoleYield 17.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of 4-[4-(3-indolyl)piperidinomethyl]-2-aminothiazole (1 g), triethylamine (1.3 g) and N,N-dimethylformamide (10 ml) was added dropwise a solution of 2-acetoxyacetyl chloride (0.87 g) in methylene chloride (1 ml) in a stream of nitrogen gas with ice-cooling and stirring over a period of 20 minutes. After 3 hours, the reaction mixture was filtered and the residue on the filter paper was washed with N,N-dimethylformamide (10 ml). The filtrate and washings were combined and concentrated under reduced pressure to remove the solvent. The residue was subjected to column chromatography on silica gel and elution was carried out with a mixture of chloroform and methanol (20:1 V/V). The fractions containing the desired compound were collected and concentrated under reduced pressure and the residue was recrystallized from a mixture of water and ethanol to give 4-[4-(3-indolyl)piperidinomethyl]-2-(2-acetoxyacetylamino)thiazole (0.23 g).

Workup

  1. temperaturecooling
  2. waitAfter 3 hours
  3. filtrationthe reaction mixture was filtered
  4. washthe residue on the filter paper was washed with N,N-dimethylformamide (10 ml)
  5. concentrationconcentrated under reduced pressure
  6. customto remove the solvent
  7. washThe residue was subjected to column chromatography on silica gel and elution
  8. additionwas carried out with a mixture of chloroform and methanol (20:1 V/V)
  9. additionThe fractions containing the desired compound
  10. customwere collected
  11. concentrationconcentrated under reduced pressure
  12. customthe residue was recrystallized from a mixture of water and ethanol

Sources & evidence

ORD record
ord-920ebc5f8f2f4d0991788163f1b23848
Source dataset
uspto-grants-1988_05
Patent number
US04742057

Reaction notes

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