Water → HCID 13755078, compound

HRID 648695Notes

Reaction equation

HRID 648695 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([CH:13]2[CH2:18][CH2:17][CH2:16][NH:15][CH2:14]2)=[C:7]2[C:11]=1[NH:10][C:9](=[O:12])[CH2:8]2.C(=O)([O-])[O-].[K+].[K+].[CH2:25](I)[CH2:26][CH3:27].O>CN(C)C=O>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([CH:13]2[CH2:18][CH2:17][CH2:16][N:15]([CH2:25][CH2:26][CH3:27])[CH2:14]2)=[C:7]2[C:11]=1[NH:10][C:9](=[O:12])[CH2:8]2

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 336431-IodopropaneHCID 13755077HCID 13755077, compound

Product 1

HCID 13755078HCID 13755078, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 2 g of the product of Example 1 in 40 ml of dimethylformamide, 3.39 g of potassium carbonate and 1.6 ml of propyl iodide was stirred under inert atmosphere for 90 minutes. After adding water, extracting with methylene chloride, washing with water, drying, evaporating to dryness under reduced pressure and purifying the residue by chromatography over silica (eluent: methylene chloride--methanol 9-1), 1.6 g of 1,3-dihydro-7-methoxy-4-(1-propyl-3-piperidinyl)-2H-indol-2-one melting at ≈120° C. were obtained.

Workup

  1. extractionextracting with methylene chloride
  2. washwashing with water
  3. customdrying
  4. customevaporating to dryness under reduced pressure
  5. custompurifying the residue by chromatography over silica (eluent: methylene chloride--methanol 9-1)

Sources & evidence

ORD record
ord-01d102f593d34c74ae0e2450b1afbce5
Source dataset
uspto-grants-1988_04
Patent number
US04736034

Reaction notes

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