Potassium Carbonate → HCID 86746446, compound

HRID 1645800Notes

Reaction equation

HRID 1645800 reaction equation
C(=O)([O-])[O-].[K+].[K+].[C:7]1([CH2:13][CH2:14][CH2:15][N:16]2[CH2:21][CH2:20][N:19](CCO)[CH2:18][CH2:17]2)[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[F:25][C:26]1[CH:31]=[CH:30][C:29]([CH:32](Cl)[C:33]2[S:34][CH:35]=[CH:36][C:37]=2[CH3:38])=[CH:28][CH:27]=1.C(O)(=O)/C=[CH:42]\[C:43](O)=[O:44]>CC(C)=O.C1(C)C=CC=CC=1.C(#N)C>[F:25][C:26]1[CH:31]=[CH:30][C:29]([CH:32]([C:33]2[S:34][CH:35]=[CH:36][C:37]=2[CH3:38])[O:44][CH2:43][CH2:42][CH:18]2[CH2:17][N:16]([CH2:15][CH2:14][CH2:13][C:7]3[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=3)[CH2:21][CH2:20][NH:19]2)=[CH:28][CH:27]=1

Participants

8

Reactant 4

HCID 11430Potassium CarbonateHCID 444266Maleic AcidHCID 782644HCID 782644, compoundHCID 19802557HCID 19802557, compound

Product 1

HCID 86746446HCID 86746446, compound

Reagents, catalysts & solvents 3

HCID 180AcetoneSolventHCID 1140TolueneSolventHCID 6342AcetonitrileSolvent2×

Procedure

3.0 g (0.022 mol) potassium carbonate were added to a stirred solution of 1.5 g (0.006 mol) 4-(3-phenylpropyl)-1-piperazineethanol (GB Pat. No. 1545094) and 2.41 g (0.010 mol) (4-fluorophenyl)(3-methyl-2-thienyl)methyl chloride (e.g. German patent appl. DE 3726068) in 50 ml acetone. The mixture was refluxed for 2 h, then cooled and diluted with toluene (100 ml). The solution was washed twice with water and once with brine. Evaporation of the organic layer in vacuo yielded an oil, which was redissolved in 50 ml acetonitrile and treated with a solution of maleic acid in acetonitrile. The precipitate was filtered off, washed with diethylether and dried. Recrystallization from ethanol gave 2.88 g (70% of theoretical yield) of the title compound as the dimaleate salt, white solid, m.p. 146°-47° C.

Workup

  1. temperatureThe mixture was refluxed for 2 h
  2. temperaturecooled
  3. washThe solution was washed twice with water and once with brine
  4. customEvaporation of the organic layer in vacuo
  5. customyielded an oil, which
  6. filtrationThe precipitate was filtered off
  7. washwashed with diethylether
  8. customdried
  9. customRecrystallization from ethanol
  10. customgave

Sources & evidence

ORD record
ord-c9ab8568163d4a87a6e509d66cc55d3b
Source dataset
uspto-grants-1993_01
Patent number
US05177077

Reaction notes

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