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

HRID 1494530Notes

Reaction equation

HRID 1494530 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][CH:11]([NH:14][C:15](=[O:30])[C:16]2[CH:21]=[C:20]([N+:22]([O-:24])=[O:23])[C:19]([NH:25]C(=O)C)=[CH:18][C:17]=2[OH:29])[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[CH2:9][CH2:10][CH:11]([NH:14][C:15](=[O:30])[C:16]2[CH:21]=[C:20]([N+:22]([O-:24])=[O:23])[C:19]([NH2:25])=[CH:18][C:17]=2[OH:29])[CH2:12][CH2:13]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 12821333N-(1-benzylpiperid-4-yl)-2-hydroxy-4-acetamido-5-nitrobenzamide

Product 1

HCID 12821334N-(1-benzylpiperid-4-yl)-2-hydroxy-4-amino-5-nitrobenzamideYield 101.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

A mixture of N-(1-benzylpiperid-4-yl)-2-hydroxy-4-acetamido-5-nitrobenzamide (1 g; 0.0024 moles) [prepared as described in Example 2], sodium hydroxide (0.2 g; 0.0048 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 precipitate collected by filtration. This precipitate was washed with water and then with diethyl ether to give 0.9 g of N-(1-benzylpiperid-4-yl)-2-hydroxy-4-amino-5-nitrobenzamide. This compound was treated with a saturated solution of hydrogen chloride in methanol to give the hydrochloride which was recrystallized from ethanol. N-(1-Benzylpiperid-4-yl)-2-hydroxy-4-amino-5-nitrobenzamide hydrochloride was obtained, m.p. 248°-250° C. (dec).

Workup

  1. temperatureunder reflux for 3 hours
  2. filtrationthe precipitate collected by filtration
  3. washThis precipitate was washed with water

Sources & evidence

ORD record
ord-ec211370fa664c4ca62ff78937ff0fb5
Source dataset
uspto-grants-1991_06
Patent number
US05026858

Reaction notes

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