Sodium Hydroxide → 1-{3-[4-(4-Chlorobenzyl)piperazin-1-yl]propyl}-3-(4-carboxyphenyl)urea hydrochloride

HRID 543174

Reaktionsgleichung

Reaktionsgleichung von HRID 543174
Cl.[Cl:2][C:3]1[CH:33]=[CH:32][C:6]([CH2:7][N:8]2[CH2:13][CH2:12][N:11]([CH2:14][CH2:15][CH2:16][NH:17][C:18]([NH:20][C:21]3[CH:26]=[CH:25][C:24]([C:27]([O:29]CC)=[O:28])=[CH:23][CH:22]=3)=[O:19])[CH2:10][CH2:9]2)=[CH:5][CH:4]=1.[OH-].[Na+]>CO>[ClH:2].[Cl:2][C:3]1[CH:4]=[CH:5][C:6]([CH2:7][N:8]2[CH2:9][CH2:10][N:11]([CH2:14][CH2:15][CH2:16][NH:17][C:18]([NH:20][C:21]3[CH:26]=[CH:25][C:24]([C:27]([OH:29])=[O:28])=[CH:23][CH:22]=3)=[O:19])[CH2:12][CH2:13]2)=[CH:32][CH:33]=1

Komponenten

4

Edukt 2

HCID 14798Sodium HydroxideHCID 202057461-{3-[4-(4-Chlorobenzyl)piperazin-1-yl]propyl}-3-(4-ethoxycarbonylphenyl)urea hydrochloride

Produkt 1

HCID 202057421-{3-[4-(4-Chlorobenzyl)piperazin-1-yl]propyl}-3-(4-carboxyphenyl)urea hydrochlorideAusbeute 146,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

A solution of 1-{3-[4-(4-chlorobenzyl)piperazin-1-yl]-propyl}-3-(4-ethoxycarbonylphenyl)urea hydrochloride (2.59 g; 5.6 mmole) in methanol (75 ml) was refluxed for 8 hours with aqueous sodium hydroxide (1N; 10 ml). The reaction mixture was concentrated in vacuo, and the residue was dissolved in water. After filtration, the solution was acidified with hydrochloric acid, and the precipitated solid was collected and washed with methanol to provide the title compound (1.92 g; 80% yield) as colorless crystals, m.p. 244°-246° C.

Aufarbeitung

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. dissolutionthe residue was dissolved in water
  3. filtrationAfter filtration
  4. customthe precipitated solid was collected
  5. washwashed with methanol

Quellen und Nachweise

ORD-Eintrag
ord-02d1ffcb85b04d64807f20945821b51c
Quelldatensatz
uspto-grants-1987_04
Patentnummer
US04661481

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