Potassium Carbonate → tert-Butyl 4-(cyanomethylidene)piperidine-1-carboxylate

HRID 470616Notes

Reaction equation

HRID 470616 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C:11](=O)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(=O)([O-])[O-].[K+].[K+].C(OP([CH2:29][C:30]#[N:31])(=O)OCC)C>C1COCC1>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C:11](=[CH:29][C:30]#[N:31])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 75676Diethyl (cyanomethyl)phosphonateHCID 735900tert-Butyl 4-oxopiperidine-1-carboxylate2×

Product 1

HCID 15326949tert-Butyl 4-(cyanomethylidene)piperidine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 4-oxo-piperidine-1-carboxylic acid tert-butyl ester (compound of Example 13; 13.5 g, 67 mmol), anhydrous potassium carbonate (11.22 g, 81 mmol) and cyanomethyl phosphonic acid diethylester (15.6 g, 88 mmol) in THF (70 mL) was heated at reflux for 12 h. THF was evaporated and the residue was dissolved in chloroform (2×50 mL). The resulting solution was washed with water (2×50 mL) and brine (50 mL). The organic phase obtained was dried over anhydrous sodium sulphate and concentrated to afford the title compound.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 12 h
  3. customTHF was evaporated
  4. dissolutionthe residue was dissolved in chloroform (2×50 mL)
  5. washThe resulting solution was washed with water (2×50 mL) and brine (50 mL)
  6. customThe organic phase obtained
  7. dry with materialwas dried over anhydrous sodium sulphate
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-395f0cda274f486ebad312f96e2a7d81
Source dataset
uspto-grants-2014_01
Patent number
US08629277B2

Reaction notes

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