Water → Hydrochloric Acid

HRID 1452327Notes

Reaction equation

HRID 1452327 reaction equation
[CH3:1][N:2]([CH2:6][C:7]1[C:16]2[O:15][C:14]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)=[C:13]([CH3:23])[C:12](=[O:24])[C:11]=2[CH:10]=[CH:9][CH:8]=1)[CH2:3][CH2:4][Cl:5].[CH3:25][O:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=1[N:33]1[CH2:38][CH2:37][NH:36][CH2:35][CH2:34]1.C(=O)([O-])[O-].[K+].[K+].O>CN(C)C=O>[ClH:5].[ClH:5].[CH3:1][N:2]([CH2:6][C:7]1[C:16]2[O:15][C:14]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)=[C:13]([CH3:23])[C:12](=[O:24])[C:11]=2[CH:10]=[CH:9][CH:8]=1)[CH2:3][CH2:4][N:36]1[CH2:35][CH2:34][N:33]([C:28]2[CH:29]=[CH:30][CH:31]=[CH:32][C:27]=2[O:26][CH3:25])[CH2:38][CH2:37]1.[ClH:5]

Participants

7

Reactant 4

HCID 962WaterHCID 13461-(2-Methoxyphenyl)piperazineHCID 11430Potassium CarbonateHCID 19972453HCID 19972453, compound

Product 2

HCID 313Hydrochloric AcidHCID 67714383HCID 67714383, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of 5.2 g of Intermediate XXVII, 3.1 g of 1-(2-methoxyphenyl)-piperazine and 2.2 g of anhydrous potassium carbonate in 50 ml of dimethylformamide was stirred at 70° C. for 7 hours. After cooling to 20°-25° C., the reaction mixture was poured into 500 ml of water, and extracted with dichloromethane. 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 ethyl acetate:petroleum ether (98:2). The title compound was obtained by salification with ethanolic hydrogen chloride. m.p. 217°-219° C.

Workup

  1. temperatureAfter cooling to 20°-25° C.
  2. extractionextracted with dichloromethane
  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 ethyl acetate:petroleum ether (98:2)

Sources & evidence

ORD record
ord-26bbf10fdd4f45c9b93ee167eb0d5680
Source dataset
uspto-grants-1997_02
Patent number
US05605896

Reaction notes

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