Potassium Carbonate → Ethyl 1-benzyl-4-(cyanomethyl)-3-oxopiperidine-4-carboxylate

HRID 1848474Notes

Reaction equation

HRID 1848474 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][CH:11]([C:14]([O:16][CH2:17][CH3:18])=[O:15])[C:10](=[O:19])[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([O-])([O-])=O.[K+].[K+].Br[CH2:27][C:28]#[N:29]>CC(C)=O>[CH2:1]([N:8]1[CH2:13][CH2:12][C:11]([CH2:27][C:28]#[N:29])([C:14]([O:16][CH2:17][CH3:18])=[O:15])[C:10](=[O:19])[CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 11534BromoacetonitrileHCID 419705Ethyl 3-oxo-1-(phenylmethyl)-4-piperidinecarboxylate

Product 1

HCID 86709485Ethyl 1-benzyl-4-(cyanomethyl)-3-oxopiperidine-4-carboxylate

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a flask charged with ethyl 1-benzyl-3-oxopiperidine-4-carboxylate (1.0 g, 3.8 mmol) and a stir bar was added K2CO3 (1.06 g, 7.6 mmol), bromoacetonitrile (0.92 g, 7.6 mmo0, and acetone (15 mL). The reaction was allowed to stir at RT for 2 hours. LC showed slow reaction. It was then heated to 45° C. for 3 hours. LC showed complete reaction at that point. The reaction was quenched with NH4Cl, extracted with EtOAc, dried over Na2SO4, filtered and concentrated. The crude product was purified by MPLC to furnish the title compound. LCMS: m/z 301 (M+H)+.

Workup

  1. customreaction
  2. temperatureIt was then heated to 45° C. for 3 hours
  3. customreaction at that point
  4. customThe reaction was quenched with NH4Cl
  5. extractionextracted with EtOAc
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe crude product was purified by MPLC

Sources & evidence

ORD record
ord-1cb8f7b72b2542d2840e9882b42b44a7
Source dataset
uspto-grants-2015_02
Patent number
US08952166B2

Reaction notes

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