Hydrochloric Acid → N-(1-benzylpiperid-4-yl)-2-hydroxy-4-acetamido-5-nitrobenzamide

HRID 1494529Notes

Reaction equation

HRID 1494529 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][CH:11]([NH:14][C:15](=[O:33])[C:16]2[CH:21]=[C:20]([N+:22]([O-:24])=[O:23])[C:19]([NH:25][C:26](=[O:28])[CH3:27])=[CH:18][C:17]=2[O:29]C(=O)C)[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+].C(O)C.Cl>O>[CH2:1]([N:8]1[CH2:13][CH2:12][CH:11]([NH:14][C:15](=[O:33])[C:16]2[CH:21]=[C:20]([N+:22]([O-:24])=[O:23])[C:19]([NH:25][C:26](=[O:28])[CH3:27])=[CH:18][C:17]=2[OH:29])[CH2:10][CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 14798Sodium HydroxideHCID 12821304N-(1-benzylpiperid-4-yl)-2-acetoxy-4-acetamido-5-nitrobenzamide

Product 1

HCID 12821333N-(1-benzylpiperid-4-yl)-2-hydroxy-4-acetamido-5-nitrobenzamideYield 86%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

A mixture of N-(1-benzylpiperid-4-yl)-2-acetoxy-4-acetamido-5-nitrobenzamide (1.4 g; 0.0031 moles) [prepared by the procedure described in Example 1], sodium hydroxide (0.3 g; 0.0062 moles), water (25 ml) and ethanol (12.5 ml) was boiled under reflux for 3 hours. Then the mixture was diluted with water, neutralized with diluted hydrochloric acid and the solid filtered off, washed with water and diethyl ether to give 1.1 g of N-(1-benzylpiperid-4-yl)-2-hydroxy-4-acetamido-5-nitrobenzamide, m.p. 220°-222° C.

Workup

  1. customprepared by the procedure
  2. temperatureunder reflux for 3 hours
  3. filtrationthe solid filtered off
  4. washwashed with water and diethyl ether

Sources & evidence

ORD record
ord-11fb798f5a7f44c09b297da217c23585
Source dataset
uspto-grants-1991_06
Patent number
US05026858

Reaction notes

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