Dichloromethane → 2-[4-(Hexadecyloxy)phenoxy]-N-(2-pyridinylmethyl)acetamide

HRID 1728866Notes

Reaction equation

[CH2:1]([O:17][C:18]1[CH:28]=[CH:27][C:21]([O:22][CH2:23][C:24](Cl)=[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(Cl)Cl.[NH2:32][CH2:33][C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][N:35]=1.C(=O)(O)[O-].[Na+]>C(Cl)(Cl)Cl.N1C=CC=CC=1>[CH2:1]([O:17][C:18]1[CH:28]=[CH:27][C:21]([O:22][CH2:23][C:24]([NH:32][CH2:33][C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][N:35]=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]

Participants

Conditions

Temperature: 0 °C

Procedure

To a 0° C. solution of 3.0 g of product from Example 87 is added 50 ml of methylene chloride, 0.829 g of 2-(aminomethyl)pyridine and 2.31 g of pyridine. The reaction is stirred at 0° C. for 3 hours; followed by 20 hours at room temperature. The mixture is poured into chloroform and saturated sodium bicarbonate. The aqueous layer is extracted with chloroform and the combined chloroform layers are washed with saturated sodium chloride, dried and concentrated in vacuo. The residue is purified by column chromatography (silica gel: 75% ethyl acetate/hexane) to give 2.90 g of the desired product as a colorless solid.

Workup

waitfollowed by 20 hours at room temperature
extractionThe aqueous layer is extracted with chloroform
washthe combined chloroform layers are washed with saturated sodium chloride
customdried
concentrationconcentrated in vacuo
customThe residue is purified by column chromatography (silica gel: 75% ethyl acetate/hexane)

Sources & evidence

ORD record: ord-756443f6f89f464ea62c9af5d438774e
Source dataset: uspto-grants-1994_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05328921

Reaction notes

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