4-(4-Chloro-benzoylamino)-4-cyano-piperidine-1-carboxylic acid tert-butyl ester → 4-Chloro-N-(4-cyano-piperidin-4-yl)-benzamide hydrochloride

HRID 913332Notes

Reaction equation

HRID 913332 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][C:11]([NH:16][C:17](=[O:25])[C:18]2[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][CH:19]=2)([C:14]#[N:15])[CH2:10][CH2:9]1)=O)(C)(C)C>Cl.O1CCOCC1>[ClH:24].[Cl:24][C:21]1[CH:22]=[CH:23][C:18]([C:17]([NH:16][C:11]2([C:14]#[N:15])[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]2)=[O:25])=[CH:19][CH:20]=1

Participants

4

Reactant 1

HCID 674023234-(4-Chloro-benzoylamino)-4-cyano-piperidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 674020814-Chloro-N-(4-cyano-piperidin-4-yl)-benzamide hydrochloride

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 312751,4-DioxaneSolvent

Procedure

A solution of 4-(4-chloro-benzoylamino)-4-cyano-piperidine-1-carboxylic acid tert-butyl ester (0.23 g, 0.63 mmol) in 4 M HCl in dioxane (30 mL) was stirred at rt for 2 h. The solvent was removed under reduced pressure and the crude product used in the consecutive step without further purification assuming quantitative deprotection and formation of the hydrochloride salt. Note: The product is contaminated with some primary amide (partial hydrolysis of the nitrile). MS (ISP): 264.1 [M+H]+.

Workup

  1. customThe solvent was removed under reduced pressure
  2. customthe crude product used in the consecutive step without further purification
  3. custompartial hydrolysis of the nitrile)

Sources & evidence

ORD record
ord-679e30291c4047d0a5d21c0d70b76cb1
Source dataset
uspto-grants-2011_09
Patent number
US08026365B2

Reaction notes

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