Hydrochloric Acid → N-cyclohexylpiperidine-4-carboxamide hydrochloride

HRID 1486729Notes

Reaction equation

HRID 1486729 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH:11]([C:14](=[O:22])[NH:15][CH:16]2[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]2)[CH2:10][CH2:9]1)=O)(C)(C)C.[ClH:23]>O1CCOCC1>[ClH:23].[CH:16]1([NH:15][C:14]([CH:11]2[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]2)=[O:22])[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 4273089N-Cyclohexyl 1-boc-piperidine-4-carboxamide

Product 1

HCID 44630870N-cyclohexylpiperidine-4-carboxamide hydrochlorideYield 99%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Conditions

Temperature
50 °C

Procedure

A solution of 4-cyclohexylcarbamoyl-piperidine-1-carboxylic acid tert-butyl ester (21.11 g, 68 mmol) in dioxane (250 mL) is treated with a 4M HCl solution in dioxane (51 ml, 204 mmol) at 0° C. for 1 h. The reaction mixture is stirred at 50° C. for 4 h. The resulting suspension is cooled down to RT and the product filtered, washed with cold dioxane (50 mL) and dried under HV. The subtitle compound (16.64 g, 99%) is obtained as a white powder; LC-MS A: tR=0.46 min; [M+H]+=211.20.

Workup

  1. temperatureThe resulting suspension is cooled down to RT
  2. filtrationthe product filtered
  3. washwashed with cold dioxane (50 mL)
  4. customdried under HV

Sources & evidence

ORD record
ord-54203706796649eb88fab358cff2b726
Source dataset
uspto-grants-2016_08
Patent number
US09428456B2

Reaction notes

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