Acetone → HCID 22636122, compound

HRID 502049Notes

Reaction equation

HRID 502049 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][NH:5][CH2:4][CH2:3]1.Cl[CH2:9][C:10]1[CH:11]=[C:12]([CH:38]=[CH:39][CH:40]=1)[C:13]([NH:15][C:16]1[CH:17]=[C:18]([CH:34]=[CH:35][C:36]=1[CH3:37])[C:19]([NH:21][C:22]1[CH:27]=[CH:26][CH:25]=[C:24]([N:28]2[CH2:33][CH2:32][O:31][CH2:30][CH2:29]2)[CH:23]=1)=[O:20])=[O:14].C(=O)([O-])[O-].[K+].[K+].CC(C)=O>C(OCC)(=O)C>[CH3:37][C:36]1[CH:35]=[CH:34][C:18]([C:19]([NH:21][C:22]2[CH:27]=[CH:26][CH:25]=[C:24]([N:28]3[CH2:29][CH2:30][O:31][CH2:32][CH2:33]3)[CH:23]=2)=[O:20])=[CH:17][C:16]=1[NH:15][C:13](=[O:14])[C:12]1[CH:38]=[CH:39][CH:40]=[C:10]([CH2:9][N:5]2[CH2:6][CH2:7][N:2]([CH3:1])[CH2:3][CH2:4]2)[CH:11]=1

Participants

6

Reactant 4

HCID 180AcetoneHCID 11430Potassium CarbonateHCID 531671-MethylpiperazineHCID 22636163HCID 22636163, compound

Product 1

HCID 22636122HCID 22636122, compoundYield 41.6%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
60 °C

Procedure

N-Methylpiperazine (0.036 g) was added to a mixture of 3-(3-chloromethylbenzamido)-4-methyl-N-(3-morpholinophenyl)benzamide (0.15 g), potassium carbonate (0.09 g) and acetone (5 ml) and the resultant mixture was stirred and heated to 60° C. for 16 hours. The mixture was evaporated and the residue was partitioned between methylene chloride and a saturated aqueous sodium bicarbonate solution. The organic phase was dried over magnesium sulphate and evaporated. The residue was purified by column chromatography on silica gel using methanol as eluent. The product so obtained was dissolved in ethyl acetate and precipitated by the addition of isohexane. There was thus obtained the title compound (0.071 g); NMR Spectrum: (DMSOd6) 2.1 (s, 3H), 2.3 (s, 3H), 2.2-2.4 (m, 8H), 3.1 (t, 4H), 3.55 (s, 2H), 3.75 (t, 4H), 6.65-6.7 (m, 1H), 7.18 (t, 1H), 7.3-7.35 (m, 1H), 7.38-7.55 (m, 4H), 7.78-7.8 (m, 1H), 7.85-7.9 (m, 2H), 7.95 (s, 1H); Mass Spectrum: M+H+ 528.

Workup

  1. customThe mixture was evaporated
  2. customthe residue was partitioned between methylene chloride
  3. dry with materialThe organic phase was dried over magnesium sulphate
  4. customevaporated
  5. customThe residue was purified by column chromatography on silica gel
  6. customThe product so obtained
  7. customprecipitated by the addition of isohexane

Sources & evidence

ORD record
ord-092cbf2e526d4ded9f2df6121dbc6d20
Source dataset
uspto-grants-2010_08
Patent number
US07772432B2

Reaction notes

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