Potassium Iodide → (+/-)-8-{3-[1-(2,3-Dihydro-1H-inden-1-yl)-4-piperidinyl]propanoyl}-1,2,5,6-tetrahydro-4H-pyrrolo[3,2,1-ij]quinolin-4-one hydrochloride

HRID 722974Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 722974
[Cl:1][CH:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3]1.[NH:11]1[CH2:16][CH2:15][CH:14]([CH2:17][CH2:18][C:19]([C:21]2[CH:22]=[C:23]3[C:28]4=[C:29]([CH2:31][CH2:32][N:27]4[C:26](=[O:33])[CH2:25][CH2:24]3)[CH:30]=2)=[O:20])[CH2:13][CH2:12]1.C(=O)([O-])[O-].[K+].[K+].[I-].[K+]>C(#N)C>[ClH:1].[CH:2]1([N:11]2[CH2:12][CH2:13][CH:14]([CH2:17][CH2:18][C:19]([C:21]3[CH:22]=[C:23]4[C:28]5=[C:29]([CH2:31][CH2:32][N:27]5[C:26](=[O:33])[CH2:25][CH2:24]4)[CH:30]=3)=[O:20])[CH2:15][CH2:16]2)[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3]1

Komponenten

6

Edukt 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 944651-Chloro-2,3-dihydro-1H-indeneHCID 99665448-[3-(4-piperidinyl)propanoyl]1,2,5,6-tetrahydro-4H-pyrrolo[3,2,1-ij]quinolin-4-one

Produkt 1

HCID 21888068(+/-)-8-{3-[1-(2,3-Dihydro-1H-inden-1-yl)-4-piperidinyl]propanoyl}-1,2,5,6-tetrahydro-4H-pyrrolo[3,2,1-ij]quinolin-4-one hydrochlorideAusbeute 27,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

1-Chloroindane (360 mg) was added to a suspension of 8-[3-(4-piperidinyl)propanoyl]1,2,5,6-tetrahydro-4H-pyrrolo[3,2,1-ij]quinolin-4-one (700 mg), potassium carbonate (700 mg) and potassium iodide (catalytic amount) in acetonitrile (10 ml) at room temperature, the mixture was stirred for 12 hours, and the reaction mixture was concentrated under reduced pressure. Water (15 ml) and ethyl acetate (20 ml) were added to the residue, and extracted with ethyl acetate. The extract was washed with brine, dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The resulting residue was purified by silica gel chromatography (eluting solvent; ethyl acetate-methanol (9:1)) to give a free base compound of the title compound as colorless crystals (285 mg) having a melting point of 111 to 113° C. The free base compound (270 mg) was treated with a hydrogen 20 chloride-ethanol solution to give, the title compound (270 mg) as pale yellow amorphous powders.

Aufarbeitung

  1. concentrationthe reaction mixture was concentrated under reduced pressure
  2. additionWater (15 ml) and ethyl acetate (20 ml) were added to the residue
  3. extractionextracted with ethyl acetate
  4. washThe extract was washed with brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customthe solvent was evaporated under reduced pressure
  7. customThe resulting residue was purified by silica gel chromatography (eluting solvent; ethyl acetate-methanol (9:1))

Quellen und Nachweise

ORD-Eintrag
ord-95dfea35738942958d2976191fe6e469
Quelldatensatz
uspto-grants-2006_11
Patentnummer
US07138533B2

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