2,2,2-Trifluoroethylhydrazine → 3,3a,4,5,6,7-Hexahydro-5-methyl-3-phenyl-7-(phenylmethylene)-2-(2,2,2-trifluoroethyl)-2H-pyrazolo[4,3-c]pyridine, hydrochloride

HRID 462253

Reaktionsgleichung

Reaktionsgleichung von HRID 462253
[ClH:1].[CH:2](=[C:9]1[C:14](=O)[C:13](=[CH:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH2:12][N:11]([CH3:23])[CH2:10]1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[F:24][C:25]([F:30])([F:29])[CH2:26][NH:27][NH2:28]>CO>[ClH:1].[CH3:23][N:11]1[CH2:10][C:9](=[CH:2][C:3]2[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=2)[C:14]2=[N:28][N:27]([CH2:26][C:25]([F:30])([F:29])[F:24])[CH:16]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[CH:13]2[CH2:12]1

Komponenten

4

Edukt 2

HCID 787402,2,2-TrifluoroethylhydrazineHCID 3587084-Piperidinone, 1-methyl-3,5-bis(phenylmethylene)-, hydrochloride

Produkt 1

HCID 1317109923,3a,4,5,6,7-Hexahydro-5-methyl-3-phenyl-7-(phenylmethylene)-2-(2,2,2-trifluoroethyl)-2H-pyrazolo[4,3-c]pyridine, hydrochlorideAusbeute 59,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

A stirred suspension of 12.5 g of 3,5-dibenzylidene-1-methyl-4-piperidone, hydrochloride in 225 ml of methanol is treated with 6.9 g of 70% aqueous 2,2,2-trifluoroethylhydrazine, heated, and the resulting solution refluxed for four hours. The solvent is removed on a rotary evaporator and the light yellow foamy residue (18 g) is dissolved in 90 ml of acetonitrile and treated with 7.5 ml of 5.1 N alcoholic hydrogen chloride; the solid salt rapidly separates after a few seconds. Following cooling for about 16 hours, the material is filtered under nitrogen, washed with cold acetonitrile and ether, and dried in vacuo yielding 9.7 g of material, melting point 185°-187° C (foaming); sintering at 181° C. Crystallization from 50 ml of methanol and 50 ml of ether yields 7.9 g of product, melting point 185°-187° C (foaming).

Aufarbeitung

  1. temperatureheated
  2. temperaturethe resulting solution refluxed for four hours
  3. customThe solvent is removed on a rotary evaporator
  4. dissolutionthe light yellow foamy residue (18 g) is dissolved in 90 ml of acetonitrile
  5. additiontreated with 7.5 ml of 5.1 N alcoholic hydrogen chloride
  6. waitthe solid salt rapidly separates after a few seconds
  7. temperatureFollowing cooling for about 16 hours
  8. filtrationthe material is filtered under nitrogen
  9. washwashed with cold acetonitrile and ether
  10. customdried in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-18ca2828380f46eea17a64b306636fae
Quelldatensatz
uspto-grants-1977_12
Patentnummer
US04065617

Verknüpfte Notizen

Wird geladen…