Acetic Acid → HCID 86657557, compound

HRID 1896279Notes

Reaction equation

HRID 1896279 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]

Participants

7

Reactant 4

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

Product 1

HCID 86657557HCID 86657557, compoundYield 32.4%

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 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-c63a0c1e39f04bbf82f7699b34ca61d2
Source dataset
uspto-grants-2013_08
Patent number
US08518948B2

Reaction notes

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