Acetic Anhydride → N-[3-(4-Piperidinomethyl-2-pyridyloxy)propyl]-2-(2-acetoxyethylthio)acetamide

HRID 52096

Reaction equation

[N:1]1([CH2:7][C:8]2[CH:13]=[CH:12][N:11]=[C:10]([O:14][CH2:15][CH2:16][CH2:17][NH:18][C:19](=[O:25])[CH2:20][S:21][CH2:22][CH2:23][OH:24])[CH:9]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[C:26](OC(=O)C)(=[O:28])[CH3:27].C(=O)([O-])O.[Na+]>N1C=CC=CC=1>[N:1]1([CH2:7][C:8]2[CH:13]=[CH:12][N:11]=[C:10]([O:14][CH2:15][CH2:16][CH2:17][NH:18][C:19](=[O:25])[CH2:20][S:21][CH2:22][CH2:23][O:24][C:26](=[O:28])[CH3:27])[CH:9]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

Conditions

Temperature: 60 °C

Procedure

0.49 g of N-[3-(4-piperidinomethyl-2-pyridyloxy)propyl]-2-(2-hydroxyethylthio)acetamide [prepared as described in step (b) above] was added to a mixture of 0.48 ml of acetic anhydride and 0.43 ml of pyridine, and the resulting mixture was warmed at 60° C. for 2 hours. At the end of this time, the reaction mixture was poured into ice-water and a saturated aqueous solution of sodium hydrogencarbonate was added to it. The resulting aqueous mixture was extracted with ethyl acetate. The extract was concentrated by evaporation under reduced pressure, and the concentrate was purified by column chromatography through silica gel, using a 1:9 by volume mixture of methanol and ethyl acetate as the eluent, to give 0.41 g (yield 75%) of the title compound as an oil.

Workup

extractionThe resulting aqueous mixture was extracted with ethyl acetate
concentrationThe extract was concentrated by evaporation under reduced pressure
customthe concentrate was purified by column chromatography through silica gel
additionby volume mixture of methanol and ethyl acetate as the eluent

Sources & evidence

ORD record: ord-528e689e82c741fab85128b6781164cd
Source dataset: uspto-grants-1997_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05616579

Linked notes

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