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

HRID 1501793Notes

Reaction equation

HRID 1501793 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-ef153468ca384a1886607c10ba134ad9
Source dataset
uspto-grants-2015_12
Patent number
US09206198B2

Reaction notes

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