Oxalic Acid → HCID 69378687, compound

HRID 605810Notes

Reaction equation

HRID 605810 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

8

Reactant 4

HCID 971Oxalic AcidHCID 79713-HydroxypyridineHCID 8028TetrahydrofuranHCID 2420851-Piperidinecarbonyl chloride

Product 1

HCID 69378687HCID 69378687, compoundYield 61.2%

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 702EthanolSolvent2×HCID 962WaterSolvent

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

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

Sources & evidence

ORD record
ord-a5ceae80815849d9a7c43858ce282778
Source dataset
uspto-grants-2011_03
Patent number
US07915261B2

Reaction notes

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