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Triethylamine → 3-((methylamino)carbonyl)-N-(2,4,6-trichlorophenyl)-1-piperazineacetamide

HRID 1638609
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1638609
[CH3:1][NH:2][C:3]([CH:5]1[CH2:10][NH:9][CH2:8][CH2:7][NH:6]1)=[O:4].Cl[CH2:12][C:13]([NH:15][C:16]1[C:21]([Cl:22])=[CH:20][C:19]([Cl:23])=[CH:18][C:17]=1[Cl:24])=[O:14].C(N(CC)CC)C>COCCO>[CH3:1][NH:2][C:3]([CH:5]1[NH:6][CH2:7][CH2:8][N:9]([CH2:12][C:13]([NH:15][C:16]2[C:17]([Cl:24])=[CH:18][C:19]([Cl:23])=[CH:20][C:21]=2[Cl:22])=[O:14])[CH2:10]1)=[O:4]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 311222-chloro-N-(2,4,6-trichlorophenyl)acetamideHCID 14722545N-Methylpiperazine-2-carboxamide

Produkt 1

HCID 147225463-((methylamino)carbonyl)-N-(2,4,6-trichlorophenyl)-1-piperazineacetamideAusbeute 24,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 80192-MethoxyethanolLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

A mixture of 15.33 parts of N-methyl-2-piperazinecarboxamide, 27.2 parts of 2-chloro-N-(2,4,6-trichlorophenyl)acetamide, 9.8 parts of N,N-diethylethanamine and 300 parts of 2-methoxyethanol was stirred for 3 hours at 60° C. The reaction mixture was evaporated. The residue was taken up in a small amount of water and treated with sodium carbonate. The product was extracted three times with dichloromethane. The combined extracts were dried, filtered and evaporated. The residue was crystallized from acetonitrile. The product was filtered off (the filtrate was set aside) and dried, yielding a first fraction of 9.27 parts (24.4%) of 3-[(methylamino)carbonyl]-N-(2,4,6-trichlorophenyl)-1-piperazineacetamide. The filtrate, which was set aside (see above) was evaporated. The residue was purified by column chromatography over silica gel using a mixture of trichloromethane and 2-propanol (90:10 by volume) as eluent. The desired fraction was collected and the eluent was evaporated. The residue was crystallized from acetonitrile. The product was filtered off and dried, yielding a second fraction of 5.93 parts (15.6%) of 3-[(methylamino)carbonyl]-N-(2,4,6-trichlorophenyl)-1-piperazineacetamide; mp. 168.9° C.

Aufarbeitung

  1. customThe reaction mixture was evaporated
  2. additiontreated with sodium carbonate
  3. extractionThe product was extracted three times with dichloromethane
  4. customThe combined extracts were dried
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue was crystallized from acetonitrile
  8. filtrationThe product was filtered off (the filtrate
  9. customdried

Quellen und Nachweise

ORD-Eintrag
ord-3c3f820f970647f2b809a74a0f883a4e
Quelldatensatz
uspto-grants-1989_11
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US04880808

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