Hydrochloric Acid → N-(4-Cyano-piperidin-4-yl)-5-methyl-nicotinamide dihydrochloride

HRID 913335Notes

Reaction equation

HRID 913335 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][C:11]([C:24]#[N:25])([NH:14][C:15]([C:17]2[CH:18]=[N:19][CH:20]=[C:21]([CH3:23])[CH:22]=2)=[O:16])[CH2:10][CH2:9]1)=O)(C)(C)C.[ClH:26]>O1CCOCC1>[ClH:26].[ClH:26].[C:24]([C:11]1([NH:14][C:15](=[O:16])[C:17]2[CH:22]=[C:21]([CH3:23])[CH:20]=[N:19][CH:18]=2)[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]1)#[N:25]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 674010464-Cyano-4-[(5-methyl-pyridine-3-carbonyl)-amino]-piperidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 67401536N-(4-Cyano-piperidin-4-yl)-5-methyl-nicotinamide dihydrochloride

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A solution of 4-cyano-4-[(5-methyl-pyridine-3-carbonyl)-amino]-piperidine-1-carboxylic acid tert-butyl ester (0.48 g, 1.39 mmol) in 4 M HCl in dioxane (7 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 dihydrochloride salt. Note: The product is contaminated with some primary amide (partial hydrolysis of the nitrile). MS (ISP): 245.4 [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-b434e00057474fb68ace538ff69fbeca
Source dataset
uspto-grants-2011_09
Patent number
US08026365B2

Reaction notes

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