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

HRID 261052Notes

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

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 962WaterSolvent

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
Patent number
US04163789

Reaction notes

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