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Hydrochloric Acid → N-(1-Cyclohexylmethylpiperid-4-yl)-2-methoxy-4-amino-5-chlorobenzamide

HRID 261052
Notes
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Reaction equation

HRID 261052 reaction equation
O.Cl.[CH:3]1([CH2:9][N:10]2[CH2:15][CH2:14][CH:13]([NH:16][C:17](=[O:31])[C:18]3[CH:23]=[C:22]([Cl:24])[C:21]([NH:25]C(=O)C)=[CH:20][C:19]=3[O:29][CH3:30])[CH2:12][CH2:11]2)[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4]1.Cl.[OH-].[Na+]>O>[CH:3]1([CH2:9][N:10]2[CH2:15][CH2:14][CH:13]([NH:16][C:17](=[O:31])[C:18]3[CH:23]=[C:22]([Cl:24])[C:21]([NH2:25])=[CH:20][C:19]=3[O:29][CH3:30])[CH2:12][CH2:11]2)[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 20395819N-(1-cyclohexylmethylpiperid-4-yl)-2-methoxy-4-acetamido-5-chlorobenzamide hydrochloride monohydrate

Product 1

HCID 20395834N-(1-Cyclohexylmethylpiperid-4-yl)-2-methoxy-4-amino-5-chlorobenzamideYield 93.4%

Reagents, catalysts & solvents 1

HCID 962
Water
Solvent

Procedure

A mixture of N-(1-cyclohexylmethylpiperid-4-yl)-2-methoxy-4-acetamido-5-chlorobenzamide hydrochloride monohydrate (10 g; 0.02 moles), concentrated hydrochloric acid (6 ml) and water (20 ml) was boiled under reflux for 1.5 hours. The solution was then made alkaline with sodium hydroxide solution and extracted with chloroform. The organic solution was dried (Na2SO4) and the solvent removed in vacuo to give N-(1-cyclohexylmethylpiperid-4-yl)-2-methoxy-4-amino-5-chlorobenzamide (7.1 g), m.p. 213°-215° C. after recrystallization from methanol.

Workup

  1. temperatureunder reflux for 1.5 hours
  2. extractionextracted with chloroform
  3. dry with materialThe organic solution was dried (Na2SO4)
  4. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-ea3189585c4543bfb2f4d3f7e4cc3f9e
Source dataset
uspto-grants-1979_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04163789

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes