4-Piperidinol, 1-methyl- → Methyl 4-[1-(1-methylpiperidin-4-yl)-2-oxo-1,2-dihydropyridin-3-yl]benzoate

HRID 910619Notes

Reaction equation

[O:1]=[C:2]1[C:7]([C:8]2[CH:17]=[CH:16][C:11]([C:12]([O:14][CH3:15])=[O:13])=[CH:10][CH:9]=2)=[CH:6][CH:5]=[CH:4][NH:3]1.[CH3:18][N:19]1[CH2:24][CH2:23][CH:22](O)[CH2:21][CH2:20]1.C(C=P(C)(C)C)#N>C1(C)C=CC=CC=1>[CH3:18][N:19]1[CH2:24][CH2:23][CH:22]([N:3]2[CH:4]=[CH:5][CH:6]=[C:7]([C:8]3[CH:17]=[CH:16][C:11]([C:12]([O:14][CH3:15])=[O:13])=[CH:10][CH:9]=3)[C:2]2=[O:1])[CH2:21][CH2:20]1

Participants

Conditions

Temperature: 100 °C

Procedure

Methyl 4-(2-oxo-1,2-dihydropyridin-3-yl)benzoate (316 mg) was suspended in toluene (7 mL), and 1-methyl-4-piperidinol (318 mg) and cyanomethylenetrimethylphosphorane (317 mg) were added thereto, followed by stirring at 100° C. for 1 hour. The reaction mixture was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (methanol/chloroform=0% to 10%) to obtain methyl 4-[1-(1-methylpiperidin-4-yl)-2-oxo-1,2-dihydropyridin-3-yl]benzoate (85 mg) as a colorless oil.

Workup

concentrationThe reaction mixture was concentrated under reduced pressure
customthe residue was purified by silica gel column chromatography (methanol/chloroform=0% to 10%)

Sources & evidence

ORD record: ord-7c156279b5404ed28763a85832a1d76a
Source dataset: uspto-grants-2011_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08022208B2

Reaction notes

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