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Hydrochloric Acid → 1-(3-Amino-benzyl)-piperidine-4-carboxylic acid cyclohexylamide

HRID 1486692
Notes
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Reaction equation

HRID 1486692 reaction equation
C(OC(=O)[NH:7][C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([CH2:14][N:15]2[CH2:20][CH2:19][CH:18]([C:21](=[O:29])[NH:22][CH:23]3[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]3)[CH2:17][CH2:16]2)[CH:9]=1)(C)(C)C.Cl.[OH-].[Na+]>O1CCOCC1>[CH:23]1([NH:22][C:21]([CH:18]2[CH2:17][CH2:16][N:15]([CH2:14][C:10]3[CH:11]=[CH:12][CH:13]=[C:8]([NH2:7])[CH:9]=3)[CH2:20][CH2:19]2)=[O:29])[CH2:24][CH2:25][CH2:26][CH2:27][CH2:28]1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 86706523[3-(4-Cyclohexylcarbamoyl-piperidin-1-ylmethyl)-phenyl]-carbamic acid tert-butyl ester

Product 1

HCID 867065241-(3-Amino-benzyl)-piperidine-4-carboxylic acid cyclohexylamide

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Conditions

Temperature
60 °C

Procedure

A solution of [3-(4-cyclohexylcarbamoyl-piperidin-1-ylmethyl)-phenyl]-carbamic acid tert-butyl ester (4.6 g, 11.1 mmol) in 1,4-dioxane (110 mL) is cooled down to 0° C. and treated with a 4N HCl solution in 1,4-dioxane (24.9 mL, 99.6 mmol). The reaction mixture is heated to 60° C. for 1 h. The reaction mixture is cooled down to RT and treated with aqueous 2N sodium hydroxide. After evaporation of 1,4-dioxane under reduced pressure the reaction mixture is extracted twice with DCM (110 mL). The combined organic phases are dried over MgSO4 and evaporated to yield the title compound as a yellowish powder: LC-MS A: tR=0.50 min; [M+H]+=316.32.

Workup

  1. temperatureThe reaction mixture is cooled down to RT
  2. customAfter evaporation of 1,4-dioxane under reduced pressure the reaction mixture
  3. extractionis extracted twice with DCM (110 mL)
  4. dry with materialThe combined organic phases are dried over MgSO4
  5. customevaporated

Sources & evidence

ORD record
ord-0d48e3b40a5c450fad1747784f1ac016
Source dataset
uspto-grants-2016_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09428456B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes