N-{2-[1-(4-fluorophenyl)-4-oxo1,3,8-triazaspiro[4,5]dec-8-yl]ethyl}-2-nitrobenzamide hydrochloride → 2-amino-N-{2-[1-(4-fluorophenyl)-4-oxo-1,3,8-triazaspiro[4,5]dec-8-yl]ethyl}benzamide

HRID 437665Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 437665
Cl.[F:2][C:3]1[CH:8]=[CH:7][C:6]([N:9]2[C:13]3([CH2:18][CH2:17][N:16]([CH2:19][CH2:20][NH:21][C:22](=[O:32])[C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=4[N+:29]([O-])=O)[CH2:15][CH2:14]3)[C:12](=[O:33])[NH:11][CH2:10]2)=[CH:5][CH:4]=1.[H][H]>[Pd].C(O)(=O)C>[NH2:29][C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][C:23]=1[C:22]([NH:21][CH2:20][CH2:19][N:16]1[CH2:15][CH2:14][C:13]2([N:9]([C:6]3[CH:7]=[CH:8][C:3]([F:2])=[CH:4][CH:5]=3)[CH2:10][NH:11][C:12]2=[O:33])[CH2:18][CH2:17]1)=[O:32]

Komponenten

5

Edukt 2

HCID 21428840N-{2-[1-(4-fluorophenyl)-4-oxo1,3,8-triazaspiro[4,5]dec-8-yl]ethyl}-2-nitrobenzamide hydrochlorideHCID 178418361HCID 178418361, Verbindung

Produkt 1

HCID 214289972-amino-N-{2-[1-(4-fluorophenyl)-4-oxo-1,3,8-triazaspiro[4,5]dec-8-yl]ethyl}benzamide

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 176Acetic AcidLösungsmittel

Versuchsvorschrift

A mixture of 9 parts of N-{2-[1-(4-fluorophenyl)-4-oxo-1,3,8-triazaspiro[4,5]dec-8-yl]ethyl}-2-nitrobenzamide hydrochloride in 150 parts of acetic acid is hydrogenated at normal pressure and at room temperature with 2 parts of palladium-on-charcoal catalyst 10%. After the calculated amount of hydrogen is taken up, the catalyst is filtered off and the filtrate is evaporated. The residue is taken up in water and the whole is alkalized with ammonium hydroxide. The product is extracted twice with trichloromethane. The combined extracts are washed twice with water, dried, filtered and evaporated. The solid residue is boiled with 2-propanol and filtered. The product is allowed to crystallize from the filtrate. It is filtered off and dried in vacuo, yielding 5 parts of 2-amino-N-{2-[1-(4-fluorophenyl)-4-oxo-1,3,8-triazaspiro[4,5]dec-8-yl]ethyl}benzamide; mp. 194.9° C.

Aufarbeitung

  1. filtrationthe catalyst is filtered off
  2. customthe filtrate is evaporated
  3. extractionThe product is extracted twice with trichloromethane
  4. washThe combined extracts are washed twice with water
  5. customdried
  6. filtrationfiltered
  7. customevaporated
  8. filtrationfiltered
  9. customto crystallize from the filtrate
  10. filtrationIt is filtered off
  11. customdried in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-ed3023a2473746faae3de178009c444f
Quelldatensatz
uspto-grants-1977_06
Patentnummer
US04031226

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