Potassium Hydroxide → HCID 67049596, compound

HRID 885871Notes

Reaction equation

HRID 885871 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:15](=[O:17])[CH3:16])[CH:5]=[C:6]([N:8]2[CH2:13][CH2:12][N:11]([CH3:14])[CH2:10][CH2:9]2)[CH:7]=1.[OH-].[K+].C([O:24][C:25](=[O:36])/[CH:26]=[CH:27]/[C:28]1[CH:33]=[CH:32][C:31]([CH:34]=O)=[CH:30][CH:29]=1)(C)(C)C>CCO.O>[Cl:1][C:2]1[CH:3]=[C:4]([C:15](=[O:17])/[CH:16]=[CH:34]/[C:31]2[CH:30]=[CH:29][C:28](/[CH:27]=[CH:26]/[C:25]([OH:36])=[O:24])=[CH:33][CH:32]=2)[CH:5]=[C:6]([N:8]2[CH2:9][CH2:10][N:11]([CH3:14])[CH2:12][CH2:13]2)[CH:7]=1

Participants

6

Reactant 3

HCID 14797Potassium HydroxideHCID 10263338HCID 10263338, compoundHCID 59733445HCID 59733445, compound

Product 1

HCID 67049596HCID 67049596, compoundYield 8.2%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
-20 °C

Procedure

A mixture of 1-[3-chloro-5-(4-methyl-piperazin-1-yl)-phenyl]-ethanone (prepared as described in Preparation 4, 300 mg, 1.19 mmol), KOH (133 mg, 2.38 mmol) and (E)-3-(4-formyl-phenyl)-acrylic acid tert-butyl ester (276 mg, 1.19 mmol) in EtOH (10 ml) and H2O (2 ml) was stirred at −20° C. for 1 h and then at room temperature for 12 h. The resulting mixture was partitioned between water and AcOEt and the organic phase was dried over Na2SO4 and evaporated in vacuo. The crude reaction mixture was purified by column chromatography (eluent: AcOEt/MeOH 9:1). The collected fractions were evaporated in vacuo and the resulting powder was dissolved in DCM (5 ml) and TFA (1 ml). The solution was stirred at room temperature for 12 h and then the solvent was removed to give 40 mg (E)-3-(4-{(E)-3-[3-chloro-5-(4-methyl-piperazin-1-yl)-phenyl]-3-oxo-propenyl}-phenyl)-acrylic acid as its trifluoroacetate salt.

Workup

  1. waitat room temperature for 12 h
  2. customThe resulting mixture was partitioned between water and AcOEt
  3. dry with materialthe organic phase was dried over Na2SO4
  4. customevaporated in vacuo
  5. customThe crude reaction mixture
  6. customwas purified by column chromatography (eluent: AcOEt/MeOH 9:1)
  7. customThe collected fractions were evaporated in vacuo
  8. dissolutionthe resulting powder was dissolved in DCM (5 ml)
  9. stirringThe solution was stirred at room temperature for 12 h
  10. customthe solvent was removed

Sources & evidence

ORD record
ord-879cd2b7bac64df38e740c91674aead8
Source dataset
uspto-grants-2012_08
Patent number
US08242175B2

Reaction notes

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