Pyridine → N-Acetyl-2-[4-(hexadecyloxy)phenoxy]-N-(2-pyridinylmethyl)acetamide

HRID 1728868Notes

Reaction equation

[CH2:1]([O:17][C:18]1[CH:35]=[CH:34][C:21]([O:22][CH2:23][C:24]([NH:26][CH2:27][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][N:29]=2)=[O:25])=[CH:20][CH:19]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16].[C:36](OC(=O)C)(=[O:38])[CH3:37].N1C=CC=CC=1>O>[C:36]([N:26]([CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][N:29]=1)[C:24](=[O:25])[CH2:23][O:22][C:21]1[CH:20]=[CH:19][C:18]([O:17][CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16])=[CH:35][CH:34]=1)(=[O:38])[CH3:37]

Participants

Conditions

Temperature: 110 °C

Procedure

A mixture of 0.70 g of product from Example 88, 2.96 g of acetic anhydride, 0.027 g of 4-N,N-dimethylaminopyridine and 15 ml of pyridine is heated at 110° C. for 35 hours and at reflux temperature for 57 hours. The reaction is poured into water and extracted with methylene chloride. The organic layer is washed with saturated sodium chloride, dried and concentrated in vacuo. The residue is purified by column chromatography (silica gel: 35% ethyl acetate/hexane) to give 0.366 g of product as light yellow crystals.

Workup

temperatureat reflux temperature for 57 hours
extractionextracted with methylene chloride
washThe organic layer is washed with saturated sodium chloride
customdried
concentrationconcentrated in vacuo
customThe residue is purified by column chromatography (silica gel: 35% ethyl acetate/hexane)

Sources & evidence

ORD record: ord-f2d6dfea9abd4172af6f6764e88f2a68
Source dataset: uspto-grants-1994_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05328921

Reaction notes

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