Water → 5-(3,4-Dichlorophenyl)-5-[2-[4-phenyl-1-azoniabicyclo[2.2.2]oct-1-yl]ethyl]-3-[3,5-bis(trifluoromethyl)benzyl]tetrahydro-2H-1,3-oxazin-2-one chloride

HRID 362722Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 362722
[C:1]1([C:7]23[CH2:14][CH2:13][N:10]([CH2:11][CH2:12]2)[CH2:9][CH2:8]3)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[F:15][C:16]([F:51])([F:50])[C:17]1[CH:18]=[C:19]([CH:43]=[C:44]([C:46]([F:49])([F:48])[F:47])[CH:45]=1)[CH2:20][N:21]1[CH2:26][C:25]([C:34]2[CH:39]=[CH:38][C:37]([Cl:40])=[C:36]([Cl:41])[CH:35]=2)([CH2:27][CH2:28]OS(C)(=O)=O)[CH2:24][O:23][C:22]1=[O:42].O.CCOCC>CN(C=O)C>[Cl-:40].[Cl:41][C:36]1[CH:35]=[C:34]([C:25]2([CH2:27][CH2:28][N+:10]34[CH2:13][CH2:14][C:7]([C:1]5[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=5)([CH2:8][CH2:9]3)[CH2:12][CH2:11]4)[CH2:24][O:23][C:22](=[O:42])[N:21]([CH2:20][C:19]3[CH:18]=[C:17]([C:16]([F:51])([F:50])[F:15])[CH:45]=[C:44]([C:46]([F:49])([F:47])[F:48])[CH:43]=3)[CH2:26]2)[CH:39]=[CH:38][C:37]=1[Cl:40]

Komponenten

6

Edukt 4

HCID 962WaterHCID 3283Diethyl EtherHCID 1428104-Phenyl-1-azabicyclo(2.2.2)octaneHCID 158866773-[3,5-Bis(trifluoromethyl)benzyl]-5-(3,4-dichlorophenyl)-5-[2-(methanesulfonyloxy)ethyl]tetrahydro-2H-1,3-oxazin-2-one

Produkt 1

HCID 195913605-(3,4-Dichlorophenyl)-5-[2-[4-phenyl-1-azoniabicyclo[2.2.2]oct-1-yl]ethyl]-3-[3,5-bis(trifluoromethyl)benzyl]tetrahydro-2H-1,3-oxazin-2-one chlorideAusbeute 24,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

A mixture of 0.53 g of 4-phenyl-1-azabicyclo-[2.2.2]octane and 1.4 g of the compound obtained in step C of EXAMPLE 4 in 5 ml of DMF is heated at 60° C. for 5 hours. After cooling to RT, the reaction mixture is poured into water and extracted with DCM, the organic phase is washed twice with 2N HCl solution and three times with saturated NaCl solution and dried over MgSO4 and the solvent is evaporated off under vacuum. The residue is chromatographed on silica using DCM and then a DCM/MeOH mixture (92/8; v/v) as the eluent. The product obtained is taken up with ether and the precipitate formed is wrung to give 0.21 g of the expected product. M.p.=138° C.

Aufarbeitung

  1. temperatureAfter cooling to RT
  2. extractionextracted with DCM
  3. washthe organic phase is washed twice with 2N HCl solution and three times with saturated NaCl solution
  4. dry with materialdried over MgSO4
  5. customthe solvent is evaporated off under vacuum
  6. customThe residue is chromatographed on silica
  7. customThe product obtained
  8. customthe precipitate formed

Quellen und Nachweise

ORD-Eintrag
ord-399068f4ee8b4dde9c0b47f267288247
Quelldatensatz
uspto-grants-1999_02
Patentnummer
US05869663

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