Potassium Carbonate → HCID 15463739, compound

HRID 1597319Notes

Reaction equation

HRID 1597319 reaction equation
[NH2:1][C:2]1[C:23]([Cl:24])=[CH:22][C:5]([C:6]([NH:8][CH:9]2[CH2:14][CH2:13][N:12]([CH2:15][CH:16]3[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]3)[CH2:11][CH2:10]2)=[O:7])=[C:4]([O:25][CH3:26])[CH:3]=1.C(=O)([O-])[O-].[K+].[K+].Cl[CH:34]([CH3:38])[C:35](=[O:37])[CH3:36]>C(#N)C>[NH2:1][C:2]1[C:23]([Cl:24])=[CH:22][C:5]([C:6]([NH:8][CH:9]2[CH2:14][CH2:13][N:12]([CH2:15][CH:16]3[CH2:17][CH2:18][N:19]([CH:34]([CH3:38])[C:35](=[O:37])[CH3:36])[CH2:20][CH2:21]3)[CH2:11][CH2:10]2)=[O:7])=[C:4]([O:25][CH3:26])[CH:3]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 200263-Chloro-2-butanoneHCID 10937790HCID 10937790, compound

Product 1

HCID 15463739HCID 15463739, compoundYield 88.6%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 4-amino-5-chloro-2-methoxy-N-[1-(4-piperidinylmethyl)-4-piperidinyl]benzamide (610 mg) in acetonitrile (30 ml) are added potassium carbonate (80 mg) and 3-chloro-2-butanone (220 mg), and the mixture is heated under reflux for 16 hours, and concentrated to dryness under reduced pressure. The residue is dissolved in chloroform, and the mixture is washed with water and a saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate, and the solvent is evaporated under reduced pressure. The residue is purified by silica gel column chromatography (eluent; chloroform:methanol=15:1) to give the desired compound (640 mg) as a yellow oily product.

Workup

  1. temperaturethe mixture is heated
  2. temperatureunder reflux for 16 hours
  3. concentrationconcentrated to dryness under reduced pressure
  4. dissolutionThe residue is dissolved in chloroform
  5. washthe mixture is washed with water
  6. dry with materiala saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate
  7. customthe solvent is evaporated under reduced pressure
  8. customThe residue is purified by silica gel column chromatography (eluent; chloroform:methanol=15:1)

Sources & evidence

ORD record
ord-4a61507fdb4c4bf5aaf328d9a1525204
Source dataset
uspto-grants-2001_09
Patent number
US06294555B1

Reaction notes

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