tert-Butyl 4-cyano-4-(2,4-dichlorophenyl)piperidine-1-carboxylate → 4-(2,4-Dichlorophenyl)-4-piperidinecarbonitrile

HRID 1167723Notes

Reaction equation

HRID 1167723 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][C:11]([C:22]#[N:23])([C:14]2[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][C:15]=2[Cl:21])[CH2:10][CH2:9]1)=O)(C)(C)C>ClCCl.FC(F)(F)C(O)=O>[Cl:21][C:15]1[CH:16]=[C:17]([Cl:20])[CH:18]=[CH:19][C:14]=1[C:11]1([C:22]#[N:23])[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]1

Participants

4

Reactant 1

HCID 49760258tert-Butyl 4-cyano-4-(2,4-dichlorophenyl)piperidine-1-carboxylate

Product 1

HCID 229935594-(2,4-Dichlorophenyl)-4-piperidinecarbonitrileYield 99.6%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

To 4-cyano-4-(2,4-dichlorophenyl)-piperidine-1-carboxylic acid tert-butyl ester (0.620 g, 1.74 mmol) in dichloromethane (5 mL), trifluoroacetic acid (2 mL) was added and the solution stirred at room temperature for 1 hour. The solution was concentrated, neutralized with 10% KOH solution and extracted into 25 ml of dichloromethane. The organic layer was dried over sodium sulfate, filtered and concentrated to give 0.442 g (99%) of 4-(2,4-dichlorophenyl)-piperidine-4-carbonitrile which was used as such for the subsequent step.

Workup

  1. concentrationThe solution was concentrated
  2. extractionextracted into 25 ml of dichloromethane
  3. dry with materialThe organic layer was dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-7c194100479b4d54a77bb5ab8508ae7d
Source dataset
uspto-grants-2003_09
Patent number
US06620815B1

Reaction notes

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