Water → HCID 24832293, compound

HRID 1452328Notes

Reaction equation

HRID 1452328 reaction equation
[C:1]([N:4]([CH2:8][C:9]1[C:18]2[O:17][C:16]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)=[C:15]([CH3:25])[C:14](=[O:26])[C:13]=2[CH:12]=[CH:11][CH:10]=1)[CH2:5][CH2:6][Cl:7])(=[O:3])[CH3:2].[CH3:27][O:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=1[N:35]1[CH2:40][CH2:39][NH:38][CH2:37][CH2:36]1.O.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[ClH:7].[C:1]([N:4]([CH2:8][C:9]1[C:18]2[O:17][C:16]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)=[C:15]([CH3:25])[C:14](=[O:26])[C:13]=2[CH:12]=[CH:11][CH:10]=1)[CH2:5][CH2:6][N:38]1[CH2:37][CH2:36][N:35]([C:30]2[CH:31]=[CH:32][CH:33]=[CH:34][C:29]=2[O:28][CH3:27])[CH2:40][CH2:39]1)(=[O:3])[CH3:2]

Participants

6

Reactant 4

HCID 962WaterHCID 13461-(2-Methoxyphenyl)piperazineHCID 11430Potassium CarbonateHCID 19972570HCID 19972570, compound

Product 1

HCID 24832293HCID 24832293, compoundYield 57.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
95 °C

Procedure

A mixture of 5 g of Intermediate XXXIII and 5.3 g of 1-(2-methoxyphenyl)-piperazine in 75 ml of dimethylformamide was stirred at 95° C. for 2 hours. After cooling to 20°-25° C., the reaction mixture was poured into 200 ml of water, made alkaline with potassium carbonate and extracted with ethyl acetate. The organic phase was washed with water and dried on anhydrous sodium sulfate. The solvent was removed in vacuo. The residue was purified by flash chromatography on silica gel, eluting with dichloromethane:methanol (100:0.2). Salification of the pure base with ethanolic hydrogen chloride and recrystallization from methanol gave 4.4 g of the title compound, melting at (200) 227°-228° C. and containing one equivalent of methanol.

Workup

  1. temperatureAfter cooling to 20°-25° C.
  2. extractionextracted with ethyl acetate
  3. washThe organic phase was washed with water
  4. dry with materialdried on anhydrous sodium sulfate
  5. customThe solvent was removed in vacuo
  6. customThe residue was purified by flash chromatography on silica gel
  7. washeluting with dichloromethane:methanol (100:0.2)
  8. customSalification of the pure base with ethanolic hydrogen chloride and recrystallization from methanol

Sources & evidence

ORD record
ord-cf66b4464f8b431c84e5a9858b15911b
Source dataset
uspto-grants-1997_02
Patent number
US05605896

Reaction notes

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