Trifluoroacetic acid → 4-(4-Chlorophenyl)piperidine-4-carbonitrile

HRID 242565Notes

Reaction equation

HRID 242565 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][C:11]([C:16]2[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][CH:17]=2)([C:14]#[N:15])[CH2:10][CH2:9]1)=O)(C)(C)C.FC(F)(F)C(O)=O>ClCCl>[Cl:22][C:19]1[CH:20]=[CH:21][C:16]([C:11]2([C:14]#[N:15])[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]2)=[CH:17][CH:18]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 49760270tert-Butyl 4-(4-chlorophenyl)-4-cyanopiperidine-1-carboxylate

Product 1

HCID 229935654-(4-Chlorophenyl)piperidine-4-carbonitrileYield 82%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a chilled solution of 4-(4-chloro-phenyl)-4-cyano-piperidine-1-carboxylic acid tert-butyl ester (315 mg, 1 mmol) in 5 ml dichloromethane was added 1 ml trifluoroacetic acid. The reaction was stirred at 0° C. for 3 hours, then concentrated under vacuum. The resulting oil was diluted with dichloromethane and washed twice with saturated aqueous sodium bicarbonate. The aqueous washings were extracted three times with dichloromethane. The combined organic layers were dried with magnesium sulfate and concentrated under vacuum to yield the title compound (180 mg, 82%).

Workup

  1. concentrationconcentrated under vacuum
  2. additionThe resulting oil was diluted with dichloromethane
  3. washwashed twice with saturated aqueous sodium bicarbonate
  4. extractionThe aqueous washings were extracted three times with dichloromethane
  5. dry with materialThe combined organic layers were dried with magnesium sulfate
  6. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-7f058022e1234bb986880efd28800d1e
Source dataset
uspto-grants-2014_02
Patent number
US08653096B2

Reaction notes

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