4-Piperidinecarboxylic acid → 5-methyl-2-piperidin-4-yl-1,3-benzoxazole

HRID 1267270Notes

Reaction equation

HRID 1267270 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[CH:4][C:3]=1[OH:9].[NH:10]1[CH2:15][CH2:14][CH:13]([C:16](O)=O)[CH2:12][CH2:11]1.[OH-].[K+]>O>[NH:10]1[CH2:15][CH2:14][CH:13]([C:16]2[O:9][C:3]3[CH:4]=[CH:5][C:6]([CH3:8])=[CH:7][C:2]=3[N:1]=2)[CH2:12][CH2:11]1

Participants

5

Reactant 3

HCID 37734-Piperidinecarboxylic acidHCID 72642-Amino-4-methylphenolHCID 14797Potassium Hydroxide

Product 1

HCID 220285125-methyl-2-piperidin-4-yl-1,3-benzoxazoleYield 83.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
180 °C

Procedure

2-Amino-4-methylphenol (400 mg) and 4-piperidinecarboxylic acid (420 mg) were mixed with polyphosphoric acid (2 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)-5-methylbenzoxazole (586 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-a261789ee8684231b460cefe8bcb09a8
Source dataset
uspto-grants-2003_04
Patent number
US06552057B2

Reaction notes

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