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

HRID 1494530Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1494530
[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

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 14798Sodium HydroxideHCID 12821333N-(1-benzylpiperid-4-yl)-2-hydroxy-4-acetamido-5-nitrobenzamide

Produkt 1

HCID 12821334N-(1-benzylpiperid-4-yl)-2-hydroxy-4-amino-5-nitrobenzamideAusbeute 101,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel2×

Versuchsvorschrift

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).

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-ec211370fa664c4ca62ff78937ff0fb5
Quelldatensatz
uspto-grants-1991_06
Patentnummer
US05026858

Notizen zur Reaktion

Wird geladen…