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Acetonitrile → Trifluoroacetic acid

HRID 1911258
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1911258
C(OC([N:8]1[CH2:13][CH2:12][CH:11]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[CH2:20][O:21]S(C2C=CC(C)=CC=2)(=O)=O)[CH2:10][CH2:9]1)=O)(C)(C)C.CC#N.C([O-])([O-])=O.[K+].[K+].[F:41][C:42]1[CH:47]=[C:46]([F:48])[CH:45]=[C:44]([F:49])[C:43]=1O.[C:51]([OH:57])([C:53]([F:56])([F:55])[F:54])=[O:52]>CC(O)=O.O>[F:41][C:42]1[CH:47]=[C:46]([F:48])[CH:45]=[C:44]([F:49])[C:43]=1[O:21][CH2:20][C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=1[CH:11]1[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]1.[C:51]([OH:57])([C:53]([F:56])([F:55])[F:54])=[O:52]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

8

Edukt 5

HCID 6342AcetonitrileHCID 6422Trifluoroacetic acidHCID 11430Potassium CarbonateHCID 5199742,4,6-TrifluorophenolHCID 462129884-[2-(Toluene-4-sulfonyloxymethyl)phenyl]piperidine-1-carboxylic acid t-butyl ester

Produkt 2

HCID 6422Trifluoroacetic acid
Ausbeute 242,6 %
HCID 46189893Ampreloxetine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 21899381Acetic acid--water (1/1)Lösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

4-[2-(Toluene-4-sulfonyloxymethyl)phenyl]piperidine-1-carboxylic acid t-butyl ester (2.1 g, 4.7 mmol, 1.0 eq.) was dissolved in MeCN (46 mL, 890 mmol) and added to K2CO3 (1.9 g, 14 mmol, 3.0 eq.) and 2,4,6-trifluorophenol (1.0 g, 7.0 mmol, 1.5 eq.). The mixture was shaken at 50° C. overnight, then cooled to room temperature. The supernatant was separated from the K2CO3 and other solids. TFA (7 mL, 90 mmol, 20.0 eq.) was added to the supernatant and the mixture was shaken overnight at room temperature. The solution was then concentrated to yield a crude residue. The residue was dissolved in 5.0 mL 1:1 AcOH/H2O, then in an additional 2.0 mL AcOH, filtered and purified by preparative HPLC to yield the title compound as a TFA salt (1.3 g, 97.5% purity). MS m/z: [M+H]+ calcd for C18H18F3NO, 322.13. found 322.2.

Aufarbeitung

  1. temperaturecooled to room temperature
  2. customThe supernatant was separated from the K2CO3 and other solids
  3. stirringthe mixture was shaken overnight at room temperature
  4. concentrationThe solution was then concentrated
  5. customto yield a crude residue
  6. filtrationin an additional 2.0 mL AcOH, filtered
  7. custompurified by preparative HPLC

Quellen und Nachweise

ORD-Eintrag
ord-8a5da5d8cd484f3494498a7a01d8ffd3
Quelldatensatz
uspto-grants-2013_12
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08604058B2

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