Water → HCID 13755078, compound

HRID 2309188Notes

Reaction equation

HRID 2309188 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), 1.6 g of 1,3-dihydro-7-methoxy-4-(1-propyl-3-piperidinyl)-2H-indol-2-one melting at ≃120° C.
  6. customwere obtained

Sources & evidence

ORD record
ord-e222dea98c224e539c38acaffac70711
Source dataset
uspto-grants-1987_09
Patent number
US04694011

Reaction notes

Loading…