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

HRID 1896280Notes

Reaction equation

HRID 1896280 reaction equation
[C:1](/[C:3](=[C:9](/[C:11]1[CH:16]=[CH:15][C:14]([N:17]2[CH2:22][CH2:21][N:20]([CH3:23])[CH2:19][CH2:18]2)=[CH:13][CH:12]=1)\[CH3:10])/[C:4]([O:6][CH2:7]C)=[O:5])#[N:2]>CO>[C:1]([CH:3]([CH:9]([C:11]1[CH:16]=[CH:15][C:14]([N:17]2[CH2:18][CH2:19][N:20]([CH3:23])[CH2:21][CH2:22]2)=[CH:13][CH:12]=1)[CH3:10])[C:4]([O:6][CH3:7])=[O:5])#[N:2]

Participants

3

Reactant 1

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

Product 1

HCID 67382550Methyl 2-cyano-3-(4-(4-methylpiperazin-1-yl)phenyl)butanoateYield 57.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

(Z)-ethyl 2-cyano-3-(4-(4-methylpiperazin-1-yl)phenyl)but-2-enoate (700 mg, 2.30 mmol) was added to a stirred mixture of Mg metal (2.10 g, 89.4 mmol) in methanol (20 ml) at 0° C. and stirred for 2 h at room temperature (reaction was activated by Mg metal, so exothermic). Then the reaction mixture was quenched with 6N HCl (20 ml) up to a clear solution was obtained. The reaction mixture was washed with ethyl acetate (2×20 ml), basified with saturated sodium bicarbonate and extracted with DCM (3×50 ml). The combined organic layer was washed with water, brine, dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure to afford 400 mg (54%) of methyl 2-cyano-3-(4-(4-methylpiperazin-1-yl)phenyl)butanoate as a colorless liquid.

Workup

  1. customreaction
  2. customThen the reaction mixture was quenched with 6N HCl (20 ml) up to a clear solution
  3. customwas obtained
  4. washThe reaction mixture was washed with ethyl acetate (2×20 ml)
  5. extractionextracted with DCM (3×50 ml)
  6. washThe combined organic layer was washed with water, brine
  7. dry with materialdried over anhydrous sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-8b430566b297438e844256d7e5600306
Source dataset
uspto-grants-2013_08
Patent number
US08518948B2

Reaction notes

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