Toluene → HCID 24803440, compound

HRID 222249Notes

Reaction equation

HRID 222249 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([C:14]([OH:16])=O)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[C:17]1(C)[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.C1N=CN(C([N:31]2[CH:35]=[N:34]C=C2)=O)C=1.C(OCC)(=O)C>O>[C:17]1([C:35]2[N:34]=[C:14]([CH:11]3[CH2:10][CH2:9][N:8]([C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:7])[CH2:13][CH2:12]3)[O:16][N:31]=2)[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

6

Reactant 4

HCID 1140TolueneHCID 8857Ethyl AcetateHCID 682631,1'-CarbonyldiimidazoleHCID 3928711-(tert-Butoxycarbonyl)-4-piperidinecarboxylic acid

Product 1

HCID 24803440HCID 24803440, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixture of 1-(tert-butoxycarbonyl)piperidine-4-carboxylic acid (5.0 g) and toluene (50 mL) was added CDI (3.9 g), followed by stirring at room temperature for 3 hours. Then, N′-hydroxybenzenecarboxyimidate (3.3 g) was added thereto, followed by stirring for 1.5 hours and then heating and refluxing for 2 hours. After leaving to be cooled, to the reaction liquid were added ethyl acetate and water, and the organic phase was separated. The organic phase was washed with water and saturated brine, and dried over magnesium sulfate, and the solvent was evaporated under reduced pressure. To the residue were added hexane and ethyl acetate, and the resulting solid was collected by filtration to obtain tert-butyl 4-(3-phenyl-1,2,4-oxadiazol-5-yl)piperidine-1-carboxylate (5.46 g).

Workup

  1. additionThen, N′-hydroxybenzenecarboxyimidate (3.3 g) was added
  2. stirringby stirring for 1.5 hours
  3. temperatureheating
  4. temperaturerefluxing for 2 hours
  5. customAfter leaving
  6. temperatureto be cooled, to the reaction liquid
  7. customthe organic phase was separated
  8. washThe organic phase was washed with water and saturated brine
  9. dry with materialdried over magnesium sulfate
  10. customthe solvent was evaporated under reduced pressure
  11. additionTo the residue were added hexane and ethyl acetate
  12. filtrationthe resulting solid was collected by filtration

Sources & evidence

ORD record
ord-65ce7df8dc2a409a8a4a4695a0cd0a6e
Source dataset
uspto-grants-2012_06
Patent number
US08207199B2

Reaction notes

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