Pyridine → N-(2-Pyridinylmethyl)-4-(tetradecyloxy)benzamide

HRID 247914

Reaktionsgleichung

[NH2:1][CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][N:4]=1.N1C=CC=CC=1.[CH2:15]([O:29][C:30]1[CH:38]=[CH:37][C:33]([C:34](Cl)=[O:35])=[CH:32][CH:31]=1)[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28]>C(Cl)Cl>[N:4]1[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=1[CH2:2][NH:1][C:34](=[O:35])[C:33]1[CH:32]=[CH:31][C:30]([O:29][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28])=[CH:38][CH:37]=1

Komponenten

Reaktionsbedingungen

Temperatur: 0 °C

Versuchsvorschrift

To a 0° C. solution of 0.674 g 2-(aminomethyl)pyridine, 20 ml methylene chloride and 1.83 ml pyridine is added, dropwise over 20 minutes, 2.0 g of product from Example 3 dissolved in 25 ml of methylene chloride. The reaction is stirred at 0° C. for 2 hours followed by stirring at room temperature for 17 hours. The reaction mixture is partitioned between chloroform and saturated sodium bicarbonate, washed with water and saturated sodium chloride, dried and concentrated in vacuo. The residue is purified by column chromatography (silica gel:75% ethyl acetate/hexane) to give 1.51 g of the desired product.

Aufarbeitung

stirringby stirring at room temperature for 17 hours
customThe reaction mixture is partitioned between chloroform and saturated sodium bicarbonate
washwashed with water and saturated sodium chloride
customdried
concentrationconcentrated in vacuo
customThe residue is purified by column chromatography (silica gel:75% ethyl acetate/hexane)

Quellen und Nachweise

ORD-Eintrag: ord-0e0c972d4a26450c9db43ea2b4fff5c1
Quelldatensatz: uspto-grants-1993_05
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US05208247

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