Hydrochloric Acid → 1-(1-Benzyl-piperidin-4-yl)-1,3-dihydro-indol-2-one

HRID 1377686

Reaktionsgleichung

Reaktionsgleichung von HRID 1377686
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][C:9]([OH:11])=O.[CH2:12]([N:19]1[CH2:24][CH2:23][C:22](=O)[CH2:21][CH2:20]1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(=O)(O)[O-].[Na+].Cl>CO.CCOCC.C(O)(=O)C>[CH2:12]([N:19]1[CH2:24][CH2:23][CH:22]([N:1]2[C:2]3[C:3](=[CH:4][CH:5]=[CH:6][CH:7]=3)[CH2:8][C:9]2=[O:11])[CH2:21][CH2:20]1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Komponenten

9

Edukt 5

HCID 313Hydrochloric AcidHCID 192201-Benzyl-4-piperidoneHCID 516892Sodium BicarbonateHCID 5837762-Aminophenylacetic acidHCID 5049666Sodium triacetoxyborohydride2×

Produkt 1

HCID 36559951-(1-Benzyl-piperidin-4-yl)-1,3-dihydro-indol-2-one

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 176Acetic AcidLösungsmittelHCID 887MethanolLösungsmittel3×HCID 3283Diethyl EtherLösungsmittel

Versuchsvorschrift

To a solution of 200 ml of methanol containing 2-aminophenylacetic acid (13.8 mmole), 1.82 ml (15.2 mmole) 1-benzyl-4-piperidone, and 4 ml acetic acid was added 20 g of 3 Angstrom molecular sieves and 1.91 g (30.4 mmole) of sodium triacetoxyborohydride at room temperature. The reaction mixture was protected from moisture and stirred overnight. After 12 hours, an additional 500 mg of sodium triacetoxyborohydride was added and stirring was continued for 4 hours more. Saturated sodium bicarbonate solution was added and most of the methanol was removed under reduced pressure. The aqueous solution was neutralized with acetic acid and extracted with ethyl acetate solution. The combined extracts were dried (sodium sulfate) and concentrated. Chromatography of the crude reaction product on silica gel (chloroform-methanol-concentrated ammonium hydroxide elution, 96:4:0.4, v/v) afforded 296 mg of a waxy solid. This material was dissolved in a solution of methanol and ether and treated with HCl gas. The resulting precipitate was collected, washed with ether and dried to give the title compound as a solid: m.p. 266°-270° C.

Aufarbeitung

  1. waitAfter 12 hours
  2. stirringstirring
  3. waitwas continued for 4 hours
  4. customwas removed under reduced pressure
  5. extractionextracted with ethyl acetate solution
  6. dry with materialThe combined extracts were dried (sodium sulfate)
  7. concentrationconcentrated
  8. customChromatography of the crude reaction product on silica gel (chloroform-methanol-concentrated ammonium hydroxide elution, 96:4:0.4, v/v)
  9. customafforded 296 mg of a waxy solid
  10. customThe resulting precipitate was collected
  11. washwashed with ether
  12. customdried

Quellen und Nachweise

ORD-Eintrag
ord-a4dd83ff9d6942bd821f18d1463155c1
Quelldatensatz
uspto-grants-1997_09
Patentnummer
US05665719

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