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

HRID 1728791Notes

Reaction equation

[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

Participants

Conditions

Temperature: 0 °C

Procedure

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 g81:75% ethyl acetate/hexane) to give 1.51 g of the desired product.

Workup

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 g81:75% ethyl acetate/hexane)

Sources & evidence

ORD record: ord-f6b7bbe909e648dfa8134c125af602fd
Source dataset: uspto-grants-1994_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05328921

Reaction notes

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