1-Chloroethyl chloroformate → 2,6-Bis(trifluoromethyl)-4-[3-(trifluoromethyl)pyrrolidin-3-yl]pyridine

HRID 1500196

Reaktionsgleichung

Reaktionsgleichung von HRID 1500196
C([N:8]1[CH2:12][CH2:11][C:10]([C:17]2[CH:22]=[C:21]([C:23]([F:26])([F:25])[F:24])[N:20]=[C:19]([C:27]([F:30])([F:29])[F:28])[CH:18]=2)([C:13]([F:16])([F:15])[F:14])[CH2:9]1)C1C=CC=CC=1.ClC(OC(Cl)C)=O>ClC(Cl)C>[F:30][C:27]([F:28])([F:29])[C:19]1[CH:18]=[C:17]([C:10]2([C:13]([F:14])([F:15])[F:16])[CH2:11][CH2:12][NH:8][CH2:9]2)[CH:22]=[C:21]([C:23]([F:24])([F:25])[F:26])[N:20]=1

Komponenten

4

Edukt 2

HCID 5213051-Chloroethyl chloroformateHCID 866749264-[1-Benzyl-3-(trifluoromethyl)pyrrolidin-3-yl]-2,6-bis(trifluoromethyl)pyridine

Produkt 1

HCID 532621872,6-Bis(trifluoromethyl)-4-[3-(trifluoromethyl)pyrrolidin-3-yl]pyridineAusbeute 70,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 63651,1-DichloroethaneLösungsmittel

Versuchsvorschrift

The solution of 4-[1-benzyl-3-(trifluoromethyl)pyrrolidin-3-yl]-2,6-bis(trifluoromethyl)pyridine (1.4 g) and 1-chloroethyl chloroformate (0.905 g) in dichloroethane was heated to reflux for 3 hours. The mixture was cooled to room temperature and then concentrated under the reduced pressure. Methanol was added to the resultant residue, which was then heated with stirring at 60° C. for two hours. The mixture was cooled to room temperature, to which was then added water. The solution was washed twice with the mixed solvent of hexane. The solution was neutralized with sodium hydroxide and then extracted with tert-butyl methyl ether three times. The organic layers were combined, washed with brine and dried over anhydrous magnesium sulfate. After the drying agent was filtered off, the solvent was removed under reduced pressure to yield 2,6-bis(trifluoromethyl)-4-[3-(trifluoromethyl)pyrrolidin-3-yl]pyridine (0.781 g).

Aufarbeitung

  1. temperatureto reflux for 3 hours
  2. concentrationconcentrated under the reduced pressure
  3. additionMethanol was added to the resultant residue, which
  4. temperaturewas then heated
  5. temperatureThe mixture was cooled to room temperature, to which
  6. washThe solution was washed twice with the mixed solvent of hexane
  7. extractionextracted with tert-butyl methyl ether three times
  8. washwashed with brine
  9. dry with materialdried over anhydrous magnesium sulfate
  10. filtrationAfter the drying agent was filtered off
  11. customthe solvent was removed under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-82dc708fb22f41fa9aab6d2cfc2d3b49
Quelldatensatz
uspto-grants-2015_12
Patentnummer
US09206122B2

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