4-Phenylpiperidin-4-ol → 1-(3-(3-(3-Ethyl-1,2,4-oxadiazol-5-yl)-9H-beta-carbolin-9-yl)-1-propyl)-4-phenylpiperidin-4-ol

HRID 355816Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 355816
Cl[CH2:2][CH2:3][CH2:4][N:5]1[C:17]2[CH:16]=[N:15][C:14]([C:18]3[O:22][N:21]=[C:20]([CH2:23][CH3:24])[N:19]=3)=[CH:13][C:12]=2[C:11]2[C:6]1=[CH:7][CH:8]=[CH:9][CH:10]=2.[C:25]1([C:31]2([OH:37])[CH2:36][CH2:35][NH:34][CH2:33][CH2:32]2)[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1>CN(C=O)C>[CH2:23]([C:20]1[N:19]=[C:18]([C:14]2[N:15]=[CH:16][C:17]3[N:5]([CH2:4][CH2:3][CH2:2][N:34]4[CH2:33][CH2:32][C:31]([C:25]5[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=5)([OH:37])[CH2:36][CH2:35]4)[C:6]4[C:11]([C:12]=3[CH:13]=2)=[CH:10][CH:9]=[CH:8][CH:7]=4)[O:22][N:21]=1)[CH3:24]

Komponenten

4

Edukt 2

HCID 963874-Phenylpiperidin-4-olHCID 110678029-(3-Chloro-1-propyl)-3-(3-ethyl-1,2,4-oxadiazol-5-yl)-9H-beta-carboline

Produkt 1

HCID 99130951-(3-(3-(3-Ethyl-1,2,4-oxadiazol-5-yl)-9H-beta-carbolin-9-yl)-1-propyl)-4-phenylpiperidin-4-olAusbeute 41,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
85 °C

Versuchsvorschrift

To a solution of Compound 3 (1.0 g, 3 mmol) in anhydrous DMF (50 mL), 4-phenylpiperidin-4-ol (0.63 g, 3.5 mmol) and TEA (1 mL) were added. The resulting mixture was heated at 85° C. for 76 h under a nitrogen atmosphere. The solvent was removed in vacuo, and the solid residue was submitted to column chromatography on silica gel with CH2Cl2 /methanol (9:1) as eluent. The purified compound was precipitated as the hydrochloride, giving the title compound (0.6 g, 36%) as an yellow solid. M.p. 169°-170° C.

Aufarbeitung

  1. customThe solvent was removed in vacuo
  2. customThe purified compound was precipitated as the hydrochloride

Quellen und Nachweise

ORD-Eintrag
ord-8e48c0dd29a94e358b1edeeab2a513a4
Quelldatensatz
uspto-grants-1998_11
Patentnummer
US05834482

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