Hydrochloric Acid → 4'-(3-chlorophenyl)spiro[3H-indole-3,3'-piperidine]-2,6'(1H)-dione

HRID 1095144Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1095144
Cl[C:2]1[CH:7]=[C:6]2[NH:8][C:9](=[O:42])[C:10]3([CH:15]([C:16]4[CH:21]=[CH:20][CH:19]=[C:18]([Cl:22])[CH:17]=4)[CH2:14][C:13](=[O:23])[NH:12][CH:11]3C3C=C(Cl)C=CC=3OC3CCC4(OCCO4)CC3)[C:5]2=[CH:4][CH:3]=1.Cl.C([O-])(O)=O.[Na+]>O1CCCC1.O>[Cl:22][C:18]1[CH:17]=[C:16]([CH:15]2[CH2:14][C:13](=[O:23])[NH:12][CH2:11][C:10]32[C:5]2[C:6](=[CH:7][CH:2]=[CH:3][CH:4]=2)[NH:8][C:9]3=[O:42])[CH:21]=[CH:20][CH:19]=1

Komponenten

6

Edukt 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 866317946-chloro-2'-[5-chloro-2-(1,4-dioxa-spiro[4.5]dec-8-yloxy)-phenyl]-4'-(3-chlorophenyl)spiro[3H-indole-3,3'-piperidine]-2,6'(1H)-dione

Produkt 1

HCID 686290234'-(3-chlorophenyl)spiro[3H-indole-3,3'-piperidine]-2,6'(1H)-dioneAusbeute 95,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of racemic(2′R, 3R, 4′S)-6-chloro-2′-[5-chloro-2-(1,4-dioxa-spiro[4.5]dec-8-yloxy)-phenyl]-4′-(3-chlorophenyl)spiro[3H-indole-3,3′-piperidine]-2,6′(1H)-dione (0.2 g, 0.32 mmol) in tetrahydrofuran (15 mL) and water (1 mL) was added aqueous HCl (2 N, 1 mL). The reaction mixture was stirred at room temperature for 1 h, then neutralized to “pH” 7 by aqueous NaHCO3 solution. The mixture was then extracted with ethyl acetate. The organic layer was separated, washed with brine, dried over MgSO4, and concentrated. The residue was purified by chromatography (EtOAc:CH2Cl2=1:1) to give racemic(2′R, 3R, 4′S)-6-chloro-2′-[5-chloro-2-cyclohexyloxy)-phenyl]-4′-(3-chlorophenyl)spiro[3H-indole-3,3′-piperidine]-2,6′(1H)-dione as a white solid (Yield 0.1 g, 54%)

Aufarbeitung

  1. extractionThe mixture was then extracted with ethyl acetate
  2. customThe organic layer was separated
  3. washwashed with brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated
  6. customThe residue was purified by chromatography (EtOAc:CH2Cl2=1:1)

Quellen und Nachweise

ORD-Eintrag
ord-2f3bd0262624468aa4962bf99ea2373b
Quelldatensatz
uspto-grants-2012_03
Patentnummer
US08134001B2

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