Tert-butyl 4-(2-cyanophenyl)piperidine-1-carboxylate → 2-(Piperidin-4-yl)benzonitrile

HRID 238269Notes

Reaction equation

HRID 238269 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH:11]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[C:20]#[N:21])[CH2:10][CH2:9]1)=O)(C)(C)C>Cl.O1CCOCC1>[NH:8]1[CH2:13][CH2:12][CH:11]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[C:20]#[N:21])[CH2:10][CH2:9]1

Participants

4

Reactant 1

HCID 18326585Tert-butyl 4-(2-cyanophenyl)piperidine-1-carboxylate

Product 1

HCID 105117772-(Piperidin-4-yl)benzonitrileYield 102.5%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 312751,4-DioxaneSolvent

Procedure

4-(2-Cyano-phenyl)-piperidine-1-carboxylic acid tert-butyl ester (0.15 g) was dissolved in a solution of hydrogen chloride in dioxane (4 M, 2 mL) and the mixture stirred for 1 hour. The solvent was evaporated under vacuum, and the resulting solid triturated from diethyl ether to give the title compound as a grey solid (0.1 g). LCMS m/z 187.2[M+H]+. R.T.=1.90 min (Analytical Method 4).

Workup

  1. customThe solvent was evaporated under vacuum
  2. customthe resulting solid triturated from diethyl ether

Sources & evidence

ORD record
ord-d340492a15624bad909f3da789d89aba
Source dataset
uspto-grants-2014_02
Patent number
US08642621B2

Reaction notes

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