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Veratric Acid → o-Methoxycarbonyl--[4-(3,4-dimethoxybenzoyl)-1-piperazinyl]acetanilide

HRID 1381192
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1381192
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][C:11]=1[O:12][CH3:13])[C:6]([OH:8])=O.C(N(CC)CC)C.ClC(OCC(C)C)=O.[CH3:29][O:30][C:31]([C:33]1[CH:48]=[CH:47][CH:46]=[CH:45][C:34]=1[NH:35][C:36](=[O:44])[CH2:37][N:38]1[CH2:43][CH2:42][NH:41][CH2:40][CH2:39]1)=[O:32]>CN(C)C=O>[CH3:29][O:30][C:31]([C:33]1[CH:48]=[CH:47][CH:46]=[CH:45][C:34]=1[NH:35][C:36](=[O:44])[CH2:37][N:38]1[CH2:43][CH2:42][N:41]([C:6](=[O:8])[C:5]2[CH:9]=[CH:10][C:11]([O:12][CH3:13])=[C:3]([O:2][CH3:1])[CH:4]=2)[CH2:40][CH2:39]1)=[O:32]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 7121Veratric AcidHCID 8471TriethylamineHCID 62365Isobutyl chloroformateHCID 13117362o-Methoxycarbonyl-alpha-(1-piperazinyl)acetanilide

Produkt 1

HCID 13117363o-Methoxycarbonyl--[4-(3,4-dimethoxybenzoyl)-1-piperazinyl]acetanilide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228
Dimethylformamide
Lösungsmittel
2×

Versuchsvorschrift

3.3 Grams of 3,4-dimethoxybenzoic acid was dissolved in 30 ml of dimethylformamide, then 2.4 g of triethylamine was added to this solution. Under ice-cooled condition, to this solution was added dropwise 2.75 g of isobutyl chloroformate with stirring, and further stirred for 30 minutes. Then to this reaction mixture was added dropwise a DMF solution containing 5.8 g of o-methoxycarbonyl-α-(1-piperazinyl)acetanilide and stirred for 5 hours. The reaction mixture was concentrated to dryness and subjected to extraction by adding chloroform and 1 N-sodium hydroxide. The chloroform layer was washed with water, dried and removed by distillation, the residue obtained was crystallized by adding ethyl acetate and the crystals formed were collected by filtration. Recrystallized from ethanol to obtain 2.3 g of o-methoxycarbonyl-α-[4-(3,4-dimethoxybenzoyl)-1-piperazinyl]acetanilide in the form of colorless needle-like crystals. Melting point: 167.5°-169.0° C.

Aufarbeitung

  1. temperatureUnder ice-cooled condition
  2. stirringfurther stirred for 30 minutes
  3. stirringstirred for 5 hours
  4. concentrationThe reaction mixture was concentrated to dryness
  5. extractionsubjected to extraction
  6. additionby adding chloroform and 1 N-sodium hydroxide
  7. washThe chloroform layer was washed with water
  8. customdried
  9. customremoved by distillation
  10. customthe residue obtained
  11. customwas crystallized
  12. additionby adding ethyl acetate
  13. customthe crystals formed
  14. filtrationwere collected by filtration
  15. customRecrystallized from ethanol

Quellen und Nachweise

ORD-Eintrag
ord-ad1ad99e703244eea37960bee29458b2
Quelldatensatz
uspto-grants-1986_04
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US04585774

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