Triphenylphosphine → Tert-butyl 4-cyanopiperidine-1-carboxylate

HRID 412582Notes

Reaction equation

HRID 412582 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([C:14](=O)[NH2:15])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>O1CCCC1.C(Cl)(Cl)(Cl)Cl>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([C:14]#[N:15])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 11776TriphenylphosphineHCID 27356461-(tert-Butoxycarbonyl)piperidine-4-carboxamide

Product 1

HCID 1514443Tert-butyl 4-cyanopiperidine-1-carboxylateYield 67.9%

Reagents, catalysts & solvents 2

HCID 5943Carbon TetrachlorideSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-carbamoylpiperidine-1-carboxylic acid tert-butyl ester (5.6 g) in a mixture of tetrahydrofuran (110 ml) and carbon tetrachloride (90 ml) was added triphenylphosphine (24.4 g), and the mixture was stirred under reflux for 1.5 hours. After completion of the reaction, the reaction mixture was filtrated and the solvent was evaporated. The obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate=3:1) and dried under reduced pressure to give the title compound (3.5 g).

Workup

  1. temperatureunder reflux for 1.5 hours
  2. customAfter completion of the reaction
  3. filtrationthe reaction mixture was filtrated
  4. customthe solvent was evaporated
  5. customThe obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate=3:1)
  6. customdried under reduced pressure

Sources & evidence

ORD record
ord-b0eeebc1b0674525b0cabf437781de79
Source dataset
uspto-grants-2003_05
Patent number
US06562828B1

Reaction notes

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