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

HRID 1252073Notes

Reaction equation

HRID 1252073 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](Cl)(=[O:38])[CH2:36][CH3:37]>C(Cl)Cl.C(Cl)(Cl)Cl.CO>[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:35](=[O:38])[CH2:36][CH3:37])[S:20][CH:21]=3)[CH2:12][CH2:11]2)=[CH:2]1

Participants

8

Reactant 4

HCID 6228DimethylformamideHCID 8471TriethylamineHCID 62324Propionyl chlorideHCID 141297964-((4-(1H-Indol-3-yl)piperidin-1-yl)methyl)thiazol-2-amine

Product 1

HCID 103169664-[4-(3-Indolyl)piperidinomethyl]-2-propionylaminothiazole

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 6212ChloroformSolventHCID 6344DichloromethaneSolvent

Procedure

To a mixture of 4-[4-(3-indolyl)piperidinomethyl]-2-aminothiazole (1.5 g), triethylamine (2.68 ml) and N,N-dimethylformamide (15 ml) was added dropwise a solution of propionyl chloride (0.63 ml) in methylene chloride (1.2 ml) over a period of 10 minutes under ice-cooling and the mixture was stirred for 4.5 hours. The reaction mixture was dissolved in a mixture of chloroform and methanol (100 ml, 10:1 V/V) and the solution was washed with water (50 ml×3) and brine (50 ml) successively, and dried over magnesium sulfate. The solvent was evaporated and the residue was subjected to column chromatography on silica gel and the column was eluted with a mixture of chloroform and methanol (30:1 to 15:1 V/V). The fractions containing the desired compound were combined and concentrated to give a residue, which was recrystallized from ethanol to give 4-[4-(3-indolyl)piperidinomethyl]-2-propionylaminothiazole (0.72 g).

Workup

  1. temperaturecooling
  2. washthe solution was washed with water (50 ml×3) and brine (50 ml) successively
  3. dry with materialdried over magnesium sulfate
  4. customThe solvent was evaporated
  5. washthe column was eluted with a mixture of chloroform and methanol (30:1 to 15:1 V/V)
  6. additionThe fractions containing the desired compound
  7. concentrationconcentrated
  8. customto give a residue, which
  9. customwas recrystallized from ethanol

Sources & evidence

ORD record
ord-057eb5a522c34af3a8b6837927866f81
Source dataset
uspto-grants-1988_05
Patent number
US04742057

Reaction notes

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