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Hydrogen chloride-ethyl acetate → N-[(3R,4R)-3-(3,4-dichlorophenyl)-1-(piperidin-4-ylcarbonyl)piperidin-4-yl]-N-methyl-3,5-bis(trifluoromethyl)benzamide Monohydrochloride

HRID 1260932
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1260932
[F:1][C:2]([F:47])([F:46])[C:3]1[CH:4]=[C:5]([C:13]([N:15]([CH3:45])[C@@H:16]2[CH2:21][CH2:20][N:19]([C:22]([CH:24]3[CH2:29][CH2:28][N:27](C(OC(C)(C)C)=O)[CH2:26][CH2:25]3)=[O:23])[CH2:18][C@H:17]2[C:37]2[CH:42]=[CH:41][C:40]([Cl:43])=[C:39]([Cl:44])[CH:38]=2)=[O:14])[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1.Cl.C(OCC)(=O)C>C(OCC)(=O)C>[ClH:43].[Cl:44][C:39]1[CH:38]=[C:37]([C@H:17]2[C@H:16]([N:15]([CH3:45])[C:13](=[O:14])[C:5]3[CH:6]=[C:7]([C:9]([F:11])([F:10])[F:12])[CH:8]=[C:3]([C:2]([F:46])([F:1])[F:47])[CH:4]=3)[CH2:21][CH2:20][N:19]([C:22]([CH:24]3[CH2:29][CH2:28][NH:27][CH2:26][CH2:25]3)=[O:23])[CH2:18]2)[CH:42]=[CH:41][C:40]=1[Cl:43]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

4

Edukt 2

HCID 21866389Hydrogen chloride-ethyl acetate2×HCID 86631298HCID 86631298, Verbindung

Produkt 1

HCID 86631339N-[(3R,4R)-3-(3,4-dichlorophenyl)-1-(piperidin-4-ylcarbonyl)piperidin-4-yl]-N-methyl-3,5-bis(trifluoromethyl)benzamide MonohydrochlorideAusbeute 177,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

To a solution of tert-butyl 4-{[(3R,4R)-4-[{[3,5-bis(trifluoromethyl)phenyl]carbonyl}(methyl)amino]-3-(3,4-dichlorophenyl)piperidin-1-yl]carbonyl}piperidine-1-carboxylate (0.502 g) obtained in Example 87 in ethyl acetate (5 mL) was added 4N hydrogen chloride/ethyl acetate (4 mL), and the mixture was stirred at 50° C. for 2 hr. The reaction mixture was concentrated under reduced pressure and the residue was dissolved in ethyl acetate. This was washed with 1N aqueous sodium hydroxide solution and dried, and the solvent was evaporated under reduced pressure. The obtained residue was treated with 1 equivalent of 4N hydrogen chloride/ethyl acetate to give the title compound (0.405 g, 89%) as a white powder.

Aufarbeitung

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. dissolutionthe residue was dissolved in ethyl acetate
  3. washThis was washed with 1N aqueous sodium hydroxide solution
  4. customdried
  5. customthe solvent was evaporated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-c6b0e2f86ba040f3a81ab71411cca828
Quelldatensatz
uspto-grants-2013_06
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08470816B2

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