Sodium Hydroxide → 5-(3,4-dihydropyran-4-yl)-3-[2-(N,N-dimethylamino)ethyl]-1H-indole

HRID 609733

Reaktionsgleichung

Reaktionsgleichung von HRID 609733
[OH-].[Na+].[O:3]1[CH:8]=[CH:7][CH:6]([C:9]2[CH:10]=[C:11]3[C:15](=[CH:16][CH:17]=2)[N:14](C(=O)C2C=CC=CC=2)[CH:13]=[C:12]3[CH2:26][CH2:27][N:28]([CH3:30])[CH3:29])[CH2:5][CH2:4]1>CO>[NH3:14].[O:3]1[CH:4]=[CH:5][CH:6]([C:9]2[CH:10]=[C:11]3[C:15](=[CH:16][CH:17]=2)[NH:14][CH:13]=[C:12]3[CH2:26][CH2:27][N:28]([CH3:29])[CH3:30])[CH2:7][CH2:8]1

Komponenten

5

Edukt 2

HCID 14798Sodium HydroxideHCID 196004485-(3,4-dihydropyran-4-yl)-3-[2-(N,N-dimethylamino)ethyl]-1-benzoylindole

Produkt 2

HCID 222AmmoniaAusbeute 10 %HCID 196004255-(3,4-dihydropyran-4-yl)-3-[2-(N,N-dimethylamino)ethyl]-1H-indoleAusbeute 141,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

An aqueous solution of sodium hydroxide (2M, 1 mL, 2 mmol) was added to 5-(3,4-dihydropyran-4-yl)-3-[2-(N,N-dimethylamino)ethyl]-1-benzoylindole (30 mg, 0.08 mmol) in methanol (2 mL) and the resulting solution was stirred at room temperature for 16 h. The reaction mixture was partitioned between water and ethyl acetate, washed with brine, dried over sodium sulfate and the solvent was removed in vacuo. Preparative thin layer chromatography (silica gel, 10% 2M methanolic ammonia in dichloromethane) yielded 5-(3,4-dihydropyran-4-yl)-3-[2-(N,N-dimethylamino)ethyl]-1H-indole (15.3 mg, 70%); HRMS-FAB+ for C17H22N2O: calculated MH+ :271.18103; found MH+ :271.18177.

Aufarbeitung

  1. customThe reaction mixture was partitioned between water and ethyl acetate
  2. washwashed with brine
  3. dry with materialdried over sodium sulfate
  4. customthe solvent was removed in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-f7644bf8f2e14e5d9929e4671f6fde81
Quelldatensatz
uspto-grants-1999_12
Patentnummer
US05998438

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