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

HRID 261053Notes

Reaction equation

HRID 261053 reaction equation
[CH:1]1([CH2:7][N:8]2[CH2:13][CH2:12][CH:11]([NH:14][C:15](=[O:32])[C:16]3[CH:21]=[C:20]([Cl:22])[C:19]([NH:23]C(=O)C(F)(F)F)=[CH:18][C:17]=3[O:30][CH3:31])[CH2:10][CH2:9]2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C(O)C.[OH-].[Na+]>O>[CH:1]1([CH2:7][N:8]2[CH2:13][CH2:12][CH:11]([NH:14][C:15](=[O:32])[C:16]3[CH:21]=[C:20]([Cl:22])[C:19]([NH2:23])=[CH:18][C:17]=3[O:30][CH3:31])[CH2:10][CH2:9]2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 702EthanolHCID 14798Sodium HydroxideHCID 20395852N-(1-cyclohexylmethylpiperid-4-yl)-2-methoxy-4-trifluoroacetamido-5-chlorobenzamide

Product 1

HCID 20395834N-(1-Cyclohexylmethylpiperid-4-yl)-2-methoxy-4-amino-5-chlorobenzamideYield 77.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of N-(1-cyclohexylmethylpiperid-4-yl)-2-methoxy-4-trifluoroacetamido-5-chlorobenzamide (8.1 g; 0.017 moles), ethanol (25 ml), water (15 ml) and 8 N sodium hydroxide aqueous solution (25 ml) was stirred for 12 hours at room temperature. After dilution with water, the mixture was extracted with chloroform and the chloroformic solution dried (Na2SO4) and evaporated in vacuo. N-(1-Cyclohexylmethylpiperid-4-yl)-2-methoxy-4-amino-5-chlorobenzamide (5 g) was obtained. It was converted into its hydrochloride by treatment with a saturated solution of ethanolic hydrogen chloride; the hydrochloride melted at 225°-227° C. (dec).

Workup

  1. extractionAfter dilution with water, the mixture was extracted with chloroform
  2. dry with materialthe chloroformic solution dried (Na2SO4)
  3. customevaporated in vacuo

Sources & evidence

ORD record
ord-8f5b826705344d14976ac03bc8e97a47
Source dataset
uspto-grants-1979_08
Patent number
US04163789

Reaction notes

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