Methanol → 7-(4-(4-(2,3-dichlorophenyl)piperazin-1-yl)butoxy)-1-(methoxymethyl)-3,4-dihydroquinolin-2(1H)-one

HRID 1971032Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1971032
[Cl:1][C:2]1[C:7]([Cl:8])=[CH:6][CH:5]=[CH:4][C:3]=1[N:9]1[CH2:14][CH2:13][N:12]([CH2:15][CH2:16][CH2:17][CH2:18][O:19][C:20]2[CH:29]=[C:28]3[C:23]([CH2:24][CH2:25][C:26](=[O:32])[N:27]3[CH2:30][OH:31])=[CH:22][CH:21]=2)[CH2:11][CH2:10]1.S(Cl)(Cl)=O.CO.[C:39]([O-])(O)=O.[Na+]>ClCCl>[Cl:1][C:2]1[C:7]([Cl:8])=[CH:6][CH:5]=[CH:4][C:3]=1[N:9]1[CH2:14][CH2:13][N:12]([CH2:15][CH2:16][CH2:17][CH2:18][O:19][C:20]2[CH:29]=[C:28]3[C:23]([CH2:24][CH2:25][C:26](=[O:32])[N:27]3[CH2:30][O:31][CH3:39])=[CH:22][CH:21]=2)[CH2:11][CH2:10]1

Komponenten

6

Edukt 4

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 516892Sodium BicarbonateHCID 58096483N-Hydroxymethyl aripiprazole

Produkt 1

HCID 580967487-(4-(4-(2,3-dichlorophenyl)piperazin-1-yl)butoxy)-1-(methoxymethyl)-3,4-dihydroquinolin-2(1H)-oneAusbeute 63 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a mixture of hemiaminal A1 (2.0 g, 4.2 mmol) in dichloromethane (20 mL) was added thionyl chloride (1.5 mL, 12.6 mmol) and stirred for 2 h at room temperature. To the reaction mixture was added methanol (10 mL) and stirred a further 2 h. The reaction poured into NaHCO3 (aq) and extracted with dichloromethane. The organic phase dried over MgSO4, evaporated and the residue purified on silica eluting with 1:1:0.1 dichloromethane/ethyl acetate/methanol to give the title compound as a cream solid (1.3 g, 63%).

Aufarbeitung

  1. stirringstirred a further 2 h
  2. extractionextracted with dichloromethane
  3. dry with materialThe organic phase dried over MgSO4
  4. customevaporated
  5. customthe residue purified on silica eluting with 1:1:0.1 dichloromethane/ethyl acetate/methanol

Quellen und Nachweise

ORD-Eintrag
ord-5a05b82a700542d584650fd66e048c21
Quelldatensatz
uspto-grants-2013_04
Patentnummer
US08431576B2

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