Potassium Hydroxide → 3-(4-Dibutylaminopropoxybenzoyl)-8-methylimidazo[1,2-a]pyridine

HRID 2350943

Reaktionsgleichung

Reaktionsgleichung von HRID 2350943
[OH:1][C:2]1[CH:19]=[CH:18][C:5]([C:6]([C:8]2[N:12]3[CH:13]=[CH:14][CH:15]=[C:16]([CH3:17])[C:11]3=[N:10][CH:9]=2)=[O:7])=[CH:4][CH:3]=1.[CH2:20]([N:24]([CH2:29][CH2:30][CH2:31]Cl)[CH2:25][CH2:26][CH2:27][CH3:28])[CH2:21][CH2:22][CH3:23].[OH-].[K+]>CO>[CH2:25]([N:24]([CH2:29][CH2:30][CH2:31][O:1][C:2]1[CH:19]=[CH:18][C:5]([C:6]([C:8]2[N:12]3[CH:13]=[CH:14][CH:15]=[C:16]([CH3:17])[C:11]3=[N:10][CH:9]=2)=[O:7])=[CH:4][CH:3]=1)[CH2:20][CH2:21][CH2:22][CH3:23])[CH2:26][CH2:27][CH3:28]

Komponenten

5

Edukt 3

HCID 14797Potassium HydroxideHCID 96084N-(3-Chloropropyl)dibutylamineHCID 142014553-(4-Hydroxybenzoyl)-8-methylimidazo[1,2-a]pyridine

Produkt 1

HCID 102737383-(4-Dibutylaminopropoxybenzoyl)-8-methylimidazo[1,2-a]pyridine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

A mixture of 3-(4-hydroxybenzoyl)-8-methylimidazo[1,2-a]pyridine (2.3 g, 9.6 mmol), dibutylaminopropyl chloride (6.8 g, 33 mmol) and potassium hydroxide (1.3 g, 23 mmol) in methanol (60 ml) was stirred at reflux for 96 hours. The mixture was concentrated and the resulting oil was flash chromatographed (silica gel, 2.5% methanol in diethyl ether) to give 1.3 g (31% yield) of the free base of the title compound. The HCl salt was prepared by dropwise addition of concentrated hydrochloric acid to a solution of the free base in methanol, concentrated and recrystallized from acetone-ether to give the HCl salt of the title compound as an off-white solid, mp 105° C. to 107° C. IR(KBr): 3440, 2640, 1645, 1605 cm-1. MS: 421 (M+). 1H NMR (CD3OD): δ 9.66 (d, J=8 Hz, 1H), 8.74 (s, 1H), 8.00-7.61 (m, 4H), 7.20 (d, J=7.2 Hz, 2H), 4.29 (t, J=5 Hz, 2H), 3.41-3.15 (m, 6H), 2.75 (s, 3H), 2.31 (m, 2 H), 1.80-1.42 (m, 8H), 1.02 (m, 6H).

Aufarbeitung

  1. temperatureat reflux for 96 hours
  2. concentrationThe mixture was concentrated
  3. customchromatographed (silica gel, 2.5% methanol in diethyl ether)

Quellen und Nachweise

ORD-Eintrag
ord-c5f6d4d100e248f3959c9540652f3b1e
Quelldatensatz
uspto-grants-1989_10
Patentnummer
US04871745

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