4-Piperidinecarboxylic acid → 2-(Piperidin-4-yl)-1,3-benzoxazole

HRID 1267269Notes

Reaction equation

HRID 1267269 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[OH:8].[NH:9]1[CH2:14][CH2:13][CH:12]([C:15](O)=O)[CH2:11][CH2:10]1.[OH-].[K+]>O>[NH:9]1[CH2:14][CH2:13][CH:12]([C:15]2[O:8][C:3]3[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=3[N:1]=2)[CH2:11][CH2:10]1

Participants

5

Reactant 3

HCID 37734-Piperidinecarboxylic acidHCID 58012-AminophenolHCID 14797Potassium Hydroxide

Product 1

HCID 7704612-(Piperidin-4-yl)-1,3-benzoxazoleYield 84.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
180 °C

Procedure

2-Aminophenol (200 mg) and 4-piperidinecarboxylic acid (236 mg) were mixed with polyphosphoric acid (1 g) and stirred with heating at 180° C. for 2 hours. After cooling to room temperature, the reaction was stopped by adding water. The filtrate was adjusted to pH 12 with 50% potassium hydroxide aqueous solution and then extracted with methylene chloride. The organic layer was washed with saturated brine and dried with magnesium sulfate, and then the solvent was evaporated under a reduced pressure to obtain the title compound 2-(4-piperidyl)benzoxazole (311.5 mg).

Workup

  1. temperatureAfter cooling to room temperature
  2. extractionextracted with methylene chloride
  3. washThe organic layer was washed with saturated brine
  4. dry with materialdried with magnesium sulfate
  5. customthe solvent was evaporated under a reduced pressure

Sources & evidence

ORD record
ord-c9c42bdc5f9f483daa870e8720699100
Source dataset
uspto-grants-2003_04
Patent number
US06552057B2

Reaction notes

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