Tert-butyl 4-(2-chlorophenyl)-4-cyanopiperidine-1-carboxylate → 4-(2-Chlorophenyl)-4-cyanopiperidine hydrochloride

HRID 238290Notes

Reaction equation

HRID 238290 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][C:11]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[Cl:22])([C:14]#[N:15])[CH2:10][CH2:9]1)=O)(C)(C)C>Cl.O1CCOCC1>[ClH:22].[Cl:22][C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=1[C:11]1([C:14]#[N:15])[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]1

Participants

4

Reactant 1

HCID 21712251Tert-butyl 4-(2-chlorophenyl)-4-cyanopiperidine-1-carboxylate

Product 1

HCID 223792744-(2-Chlorophenyl)-4-cyanopiperidine hydrochlorideYield 177.5%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 312751,4-DioxaneSolvent

Procedure

4-(2-Chloro-phenyl)-4-cyano-piperidine-1-carboxylic acid tert-butyl ester (0.25 g, 0.78 mmol) was dissolved in a solution of hydrogen chloride in dioxane (4 N, 1 mL). The mixture was stirred for 1 hour and the solvent removed by evaporation under vacuum. The solid was triturated from ether to afford the title compound as a yellow solid (0.178 g). LCMS m/z 221.2 [M+H]+. R.T.=2.18 min (Analytical Method 4).

Workup

  1. customthe solvent removed by evaporation under vacuum
  2. customThe solid was triturated from ether

Sources & evidence

ORD record
ord-371486ddcf32482fbea4b5fbf2ecbbe2
Source dataset
uspto-grants-2014_02
Patent number
US08642621B2

Reaction notes

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