Hydrochloric Acid → 4-Benzyl-6-(3,4-dichlorophenyl)-6-[2-[4-phenyl-4-(pyrrolidin-1-ylcarbonyl)piperid-1-yl]ethyl]morpholin-3-one hydrochloride monohydrate

HRID 1066662Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1066662
O.Cl.C(N1CC(C2C=CC([Cl:37])=C(Cl)C=2)(CCN2CCC(O)(C3C=CC=CC=3)CC2)[O:13]CC1=O)C1C=CC=CC=1.[CH2:40]([N:47]1[CH2:52][C:51]([CH2:61][CH2:62]N2CCC(C3C=CC=CC=3)(O)CC2)([C:53]2[CH:58]=[CH:57][C:56]([Cl:59])=[C:55]([Cl:60])[CH:54]=2)[O:50][CH2:49][C:48]1=[O:76])[C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1.Cl.[C:78]1([C:84]2([C:90]([N:92]3[CH2:96][CH2:95][CH2:94][CH2:93]3)=[O:91])[CH2:89][CH2:88][NH:87][CH2:86][CH2:85]2)[CH:83]=[CH:82][CH:81]=[CH:80][CH:79]=1.C([O-])([O-])=O.[K+].[K+].Cl>CN(C=O)C.C(Cl)Cl.CCOCC.O>[OH2:13].[ClH:37].[CH2:40]([N:47]1[CH2:52][C:51]([C:53]2[CH:58]=[CH:57][C:56]([Cl:59])=[C:55]([Cl:60])[CH:54]=2)([CH2:61][CH2:62][N:87]2[CH2:88][CH2:89][C:84]([C:78]3[CH:79]=[CH:80][CH:81]=[CH:82][CH:83]=3)([C:90]([N:92]3[CH2:96][CH2:95][CH2:94][CH2:93]3)=[O:91])[CH2:85][CH2:86]2)[O:50][CH2:49][C:48]1=[O:76])[C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1

Komponenten

9

Edukt 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 30194854-Phenyl-4-(pyrrolidin-1-ylcarbonyl)piperidineHCID 1317226224-Benzyl-6-(3,4-dichlorophenyl)-6-[2-(4-hydroxy-4-phenylpiperid-1-yl)ethyl]morpholin-3-one hydrochloride hemihydrate

Produkt 1

HCID 212005114-Benzyl-6-(3,4-dichlorophenyl)-6-[2-[4-phenyl-4-(pyrrolidin-1-ylcarbonyl)piperid-1-yl]ethyl]morpholin-3-one hydrochloride monohydrateAusbeute 74,3 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 962WaterLösungsmittelHCID 3283Diethyl EtherLösungsmittelHCID 6228DimethylformamideLösungsmittelHCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

A mixture of 0.98 g of the compound obtained in step B of EXAMPLE 14, 0.645 g of 4-phenyl-4-(pyrrolidin-1-ylcarbonyl)piperidine and 0.69 g of K2CO3 in 3 ml of DMF is heated at 80° C. for 2 hours. After cooling to RT, the reaction mixture is poured into water and extracted with an AcOEt/ether mixture, the organic phase is washed with water and dried over MgSO4 and the solvent is evaporated off under vacuum. The residue is chromatographed on silica H using a DCM/MeOH mixture (100/2; v/v) as the eluent. The product obtained is dissolved in the minimum amount of DCM and acidified to pH 1 by the addition of a saturated solution of gaseous HCl in ether and the precipitate formed is wrung to give 0.42 g of the expected product. M.p.=155-178° C.

Aufarbeitung

  1. temperatureAfter cooling to RT
  2. extractionextracted with an AcOEt/ether mixture
  3. washthe organic phase is washed with water
  4. dry with materialdried over MgSO4
  5. customthe solvent is evaporated off under vacuum
  6. customThe residue is chromatographed on silica H
  7. customThe product obtained
  8. customthe precipitate formed

Quellen und Nachweise

ORD-Eintrag
ord-ea5ade083bc64183ae879f2cf250d836
Quelldatensatz
uspto-grants-2001_06
Patentnummer
US06242637B1

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