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Dimethylformamide → HCID 15623996, Verbindung

HRID 330539
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 330539
[H-].[Na+].CN(C)C=O.[NH:8]1[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=2[N:10]=[C:9]1[NH:17][CH:18]1[CH2:23][CH2:22][N:21]([C:24]([O:26][CH2:27][CH3:28])=[O:25])[CH2:20][CH2:19]1.Cl[CH2:30][C:31]1[CH:35]=[CH:34][O:33][C:32]=1[CH3:36]>O>[CH3:36][C:32]1[O:33][CH:34]=[CH:35][C:31]=1[CH2:30][N:8]1[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=2[N:10]=[C:9]1[NH:17][CH:18]1[CH2:23][CH2:22][N:21]([C:24]([O:26][CH2:27][CH3:28])=[O:25])[CH2:20][CH2:19]1
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Komponenten

6

Edukt 4

HCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 30184551-Piperidinecarboxylic acid, 4-(1H-benzimidazol-2-ylamino)-, ethyl esterHCID 123681693-(Chloromethyl)-2-methylfuran

Produkt 1

HCID 15623996HCID 15623996, VerbindungAusbeute 19 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962
Water
Lösungsmittel

Versuchsvorschrift

To a stirred mixture of 4.6 parts of a sodium hydride dispersion 50% and 450 parts of N,N-dimethylformamide were added portionwise 57.6 parts of ethyl 4-(1H-benzimidazol-2-ylamino)-1-piperidinecarboxylate under nitrogen atmosphere. Upon complete addition, stirring was continued for 30 minutes at room temperature. 27.0 Parts of 3-(chloromethyl)-2-methylfuran were added dropwise while cooling. Upon completion, stirring was continued for 1 hour. Water was added dropwise to the mixture and the product was extracted with 4-methyl-2-pentanone. The extract was dried, filtered and evaporated. The residue was stirred in 1,1'-oxybisethane. The solid product was filtered off and purified by column chromatography over silica gel using a mixture of trichloromethane and methanol (95:5 by volume) as eluent. The pure fractions were collected and the eluent was evaporated. The residue was stirred in 1,1'-oxybisethane. The product was filtered off and dried, yielding 37.5 parts (19.0%) of ethyl 4-[[1-[(2-methyl-3-furanyl)methyl]-1H-benzimidazol-2-yl]amino]-1-piperidinecarboxylate; mp. 150.4° C. (int. 23).

Aufarbeitung

  1. additionUpon complete addition
  2. temperaturewhile cooling
  3. stirringUpon completion, stirring
  4. waitwas continued for 1 hour
  5. extractionthe product was extracted with 4-methyl-2-pentanone
  6. customThe extract was dried
  7. filtrationfiltered
  8. customevaporated
  9. stirringThe residue was stirred in 1,1'-oxybisethane
  10. filtrationThe solid product was filtered off
  11. custompurified by column chromatography over silica gel using
  12. additiona mixture of trichloromethane and methanol (95:5 by volume) as eluent
  13. customThe pure fractions were collected
  14. customthe eluent was evaporated
  15. stirringThe residue was stirred in 1,1'-oxybisethane
  16. filtrationThe product was filtered off
  17. customdried

Quellen und Nachweise

ORD-Eintrag
ord-a0ad0d50da26444f9c0508043f3308cf
Quelldatensatz
uspto-grants-1990_01
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US04897401

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