Oxalic Acid → HCID 69378687, compound

HRID 2074316Notes

Reaction equation

[OH:1][C:2]1[CH:3]=[N:4][CH:5]=[CH:6][CH:7]=1.C1COCC1.[N:13]1([C:19](Cl)=[O:20])[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]1.[C:22]([OH:27])(=[O:26])[C:23]([OH:25])=[O:24]>CN(C1C=CN=CC=1)C.C(O)C.O>[C:22]([OH:27])(=[O:26])[C:23]([OH:25])=[O:24].[N:4]1[CH:5]=[CH:6][CH:7]=[C:2]([O:1][C:19]([N:13]2[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]2)=[O:20])[CH:3]=1

Participants

Conditions

Temperature: 60 °C

Procedure

3-Hydroxypyridine (400 mg), TEA (1.17 ml) and DMAP (catalytic amount) were added in that order to a THF (10 ml) solution containing piperidine-1-carbonyl chloride (745 mg), and then heated at 60° C. for 5 hours. The reaction solution was cooled, then water (3 ml) was added thereto, and extracted with EtOAc. The extract was washed with water, and then dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (eluent: hexane:EtOAc=1:1 (v/v)) to obtain a colorless oil. The resulting oil was dissolved in ethanol, and an ethanol solution of oxalic acid (378 mg) added thereto to obtain a colorless powder. This was recrystallized from hexane/ethanol to obtain (pyridin-3-yl)piperidine-1-carboxylate oxalate (761 mg).

Workup

temperatureThe reaction solution was cooled
extractionextracted with EtOAc
washThe extract was washed with water
dry with materialdried over anhydrous magnesium sulfate
customThe solvent was evaporated under reduced pressure
customthe residue was purified by silica gel column chromatography (eluent: hexane:EtOAc=1:1 (v/v))
customto obtain a colorless oil
customto obtain a colorless powder
customThis was recrystallized from hexane/ethanol

Sources & evidence

ORD record: ord-da07a447a13b44e5a349118da5f26bb7
Source dataset: uspto-grants-2011_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07919495B2

Reaction notes

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