Trifluoroacetic acid → 4-(4-Chlorophenyl)piperidine-4-carbonitrile

HRID 457080Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 457080
C(OC([N:8]1[CH2:13][CH2:12][C:11]([C:16]2[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][CH:17]=2)([C:14]#[N:15])[CH2:10][CH2:9]1)=O)(C)(C)C.FC(F)(F)C(O)=O>ClCCl>[Cl:22][C:19]1[CH:20]=[CH:21][C:16]([C:11]2([C:14]#[N:15])[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]2)=[CH:17][CH:18]=1

Komponenten

4

Edukt 2

HCID 6422Trifluoroacetic acidHCID 49760270tert-Butyl 4-(4-chlorophenyl)-4-cyanopiperidine-1-carboxylate

Produkt 1

HCID 229935654-(4-Chlorophenyl)piperidine-4-carbonitrileAusbeute 82 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a chilled solution of 4-(4-chloro-phenyl)-4-cyano-piperidine-1-carboxylic acid tert-butyl ester (315 mg, 1 mmol) in 5 ml dichloromethane was added 1 ml trifluoroacetic acid. The reaction was stirred at 0° C. for 3 hours, then concentrated under vacuum. The resulting oil was diluted with dichloromethane and washed twice with saturated aqueous sodium bicarbonate. The aqueous washings were extracted three times with dichloromethane. The combined organic layers were dried with magnesium sulfate and concentrated under vacuum to yield the title compound (180 mg, 82%).

Aufarbeitung

  1. concentrationconcentrated under vacuum
  2. additionThe resulting oil was diluted with dichloromethane
  3. washwashed twice with saturated aqueous sodium bicarbonate
  4. extractionThe aqueous washings were extracted three times with dichloromethane
  5. dry with materialThe combined organic layers were dried with magnesium sulfate
  6. concentrationconcentrated under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-0f3f3fcb8b4449609c330ba1037058d0
Quelldatensatz
uspto-grants-2007_03
Patentnummer
US07186729B2

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