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Acetic Acid → (Z)-ethyl 2-cyano-3-(4-(4-methylpiperazin-1-yl)phenyl)but-2-enoate

HRID 2176914
Notes
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Reaction equation

HRID 2176914 reaction equation
[CH3:1][CH2:2][O:3][C:4]([CH2:6][C:7]#[N:8])=[O:5].C([O-])(=O)C.[NH4+].C(O)(=O)C.[CH3:18][N:19]1[CH2:24][CH2:23][N:22]([C:25]2[CH:30]=[CH:29][C:28]([C:31](=O)[CH3:32])=[CH:27][CH:26]=2)[CH2:21][CH2:20]1>C1C=CC=CC=1.O>[C:7](/[C:6](=[C:31](/[C:28]1[CH:27]=[CH:26][C:25]([N:22]2[CH2:21][CH2:20][N:19]([CH3:18])[CH2:24][CH2:23]2)=[CH:30][CH:29]=1)\[CH3:32])/[C:4]([O:3][CH2:2][CH3:1])=[O:5])#[N:8]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 7764Ethyl cyanoacetateHCID 335514-(4-Methyl-1-piperazinyl)acetophenoneHCID 517165Ammonium Acetate

Product 1

HCID 86657557(Z)-ethyl 2-cyano-3-(4-(4-methylpiperazin-1-yl)phenyl)but-2-enoateYield 32.4%

Reagents, catalysts & solvents 2

HCID 241
Benzene
Solvent
HCID 962WaterSolvent

Conditions

Temperature
137.5 °C

Procedure

Ethyl cyano acetate (3.12 g, 27.6 mmol), ammonium acetate (123 mg, 1.76 mmol), acetic acid (0.2 ml, 3.5 mmol) were added successively to a stirred solution of 1-(4-(4-methylpiperazin-1-yl)phenyl)ethanone (5.0 g, 23 mmol) in benzene (25 ml) and stirred for 36 h at 135-140° C. The reaction mixture was poured into water and extracted with ethyl acetate. The combined organic layer was washed with brine, dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure to give the crude product. This was purified by column chromatography using 2% methanol in CHCl3 as eluent to afford (Z)-ethyl 2-cyano-3-(4-(4-methylpiperazin-1-yl)phenyl)but-2-enoate as yellow liquid 2.30 g (32.4%).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe combined organic layer was washed with brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customto give the crude product
  7. customThis was purified by column chromatography

Sources & evidence

ORD record
ord-d55d6f5570954d8ea54cf21a1171517d
Source dataset
uspto-grants-2015_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09067888B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes