Pyridine → (7-(4-(4-(2,3-dichlorophenyl)piperazin-1-yl)butoxy)-2-oxo-3,4-dihydroquinolin-1(2H)-yl)methyl butyrate

HRID 43238

Reaktionsgleichung

Reaktionsgleichung von HRID 43238
[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.N1C=CC=CC=1.[C:39](Cl)(=[O:43])[CH2:40][CH2:41][CH3:42]>ClCCl>[C:39]([O:31][CH2:30][N:27]1[C:28]2[C:23](=[CH:22][CH:21]=[C:20]([O:19][CH2:18][CH2:17][CH2:16][CH2:15][N:12]3[CH2:13][CH2:14][N:9]([C:3]4[CH:4]=[CH:5][CH:6]=[C:7]([Cl:8])[C:2]=4[Cl:1])[CH2:10][CH2:11]3)[CH:29]=2)[CH2:24][CH2:25][C:26]1=[O:32])(=[O:43])[CH2:40][CH2:41][CH3:42]

Komponenten

5

Edukt 3

HCID 1049PyridineHCID 8855Butyryl chlorideHCID 58096483N-Hydroxymethyl aripiprazole

Produkt 1

HCID 49854924(7-(4-(4-(2,3-dichlorophenyl)piperazin-1-yl)butoxy)-2-oxo-3,4-dihydroquinolin-1(2H)-yl)methyl butyrateAusbeute 95 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a stirred suspension of Compound 2A (3 g, 6.27 mmol) in dichloromethane (30 mL) was added pyridine (2.54 mL, 31.35 mmol) followed by butyryl chloride (0.98 mL, 9.41 mmol) over 1-2 mins. The resultant solution was stirred at room temperature for 1 h 30 mins. The reaction was quenched with methanol (2 mL) and the mixture diluted with 1:1 NaHCO3 (aq)/brine (50 mL) and the layers separated. The aqueous layer was extracted with dichloromethane (10 mL) and the combined organics dried over MgSO4. After filtration, the volatiles were removed and the residue azeotroped with toluene (3×10 mL). The crude material was purified by silica chromatography eluting 8% Methanol/(1:1 ethyl acetate/dichloromethane) to provide the desired product, Compound 2B (3.26 g, 5.94 mmol, 95% yield).

Aufarbeitung

  1. customThe reaction was quenched with methanol (2 mL)
  2. additionthe mixture diluted with 1:1 NaHCO3 (aq)/brine (50 mL)
  3. customthe layers separated
  4. extractionThe aqueous layer was extracted with dichloromethane (10 mL)
  5. dry with materialthe combined organics dried over MgSO4
  6. filtrationAfter filtration
  7. customthe volatiles were removed
  8. customthe residue azeotroped with toluene (3×10 mL)
  9. customThe crude material was purified by silica chromatography
  10. washeluting 8% Methanol/(1:1 ethyl acetate/dichloromethane)

Quellen und Nachweise

ORD-Eintrag
ord-bd92cf07e5824e099a26c573bbdce9f2
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08536328B2

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