4-Piperidinecarboxylic acid → HCID 58270689, compound

HRID 222242Notes

Reaction equation

HRID 222242 reaction equation
[CH3:1][C:2]1[N:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.C1N=CN([C:14]([N:16]2[CH:20]=N[CH:18]=[CH:17]2)=[O:15])C=1.N1CC[CH:24]([C:25]([OH:27])=[O:26])[CH2:23]C1.FC(F)(F)C(O)=O>[Cl-].[Na+].O.C(Cl)(Cl)Cl.CS(C)=O>[CH3:1][C:2]1[N:7]=[CH:6][C:5]([O:8][C:14]([N:16]2[CH2:17][CH2:18][CH:24]([C:25]([OH:27])=[O:26])[CH2:23][CH2:20]2)=[O:15])=[CH:4][CH:3]=1

Participants

8

Reactant 4

HCID 37734-Piperidinecarboxylic acidHCID 6422Trifluoroacetic acidHCID 142752-Methyl-5-hydroxypyridineHCID 682631,1'-Carbonyldiimidazole

Product 1

HCID 58270689HCID 58270689, compoundYield 81.6%

Reagents, catalysts & solvents 3

HCID 679Dimethyl SulfoxideSolvent2×HCID 6212ChloroformSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

To a mixture of 6-methylpyridin-3-ol (1.8 g), CDI (2.64 g), and DMSO (18 mL) were added dropwise isonipecotic acid (4.2 g), and a mixture of DMSO (18 mL) and trifluoroacetic acid (2.5 mL), followed by stirring at room temperature for 1 day. To the reaction liquid were added saturated brine and chloroform, and the organic phase was separated. The organic phase was washed with saturated brine twice and then dried over anhydrous sodium sulfate, and the solvent was concentrated under reduced pressure. To the residue was added diisopropyl ether/methanol, and the resulting solid was collected by filtration and dried to obtain 1-{[(6-methylpyridin-3-yl)oxy]carbonyl}piperidine-4-carboxylic acid (3.51 g) as a colorless solid.

Workup

  1. customTo the reaction liquid
  2. customthe organic phase was separated
  3. washThe organic phase was washed with saturated brine twice
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationthe solvent was concentrated under reduced pressure
  6. additionTo the residue was added diisopropyl ether/methanol
  7. filtrationthe resulting solid was collected by filtration
  8. customdried

Sources & evidence

ORD record
ord-3e94052690c6495eb032e4efa4225ad6
Source dataset
uspto-grants-2012_06
Patent number
US08207199B2

Reaction notes

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