Water → 5-Chloro-2-(piperidin-1-yl)-1,3-benzoxazole

HRID 378880Notes

Reaction equation

HRID 378880 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[OH:9].[NH:10]1[CH2:15][CH2:14][CH:13](C(O)=O)[CH2:12][CH2:11]1.O.[OH-].[K+].[C:22]1(C)C(C)=CC=CC=1>>[Cl:8][C:6]1[CH:5]=[CH:4][C:3]2[O:9][C:22]([N:10]3[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15]3)=[N:1][C:2]=2[CH:7]=1

Participants

6

Reactant 5

HCID 962WaterHCID 37734-Piperidinecarboxylic acidHCID 7237O-XyleneHCID 72652-Amino-4-chlorophenolHCID 14797Potassium Hydroxide

Product 1

HCID 2302965-Chloro-2-(piperidin-1-yl)-1,3-benzoxazole

Conditions

Temperature
180 °C

Procedure

2-Amino-4-chlorophenol (400 mg) and 4-piperidinecarboxylic acid (360 mg) were mixed with polyphosphate (2 g) in xylene (30 ml) 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 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 5-chloro-2-(1-piperidyl)benzoxazole (218 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-00dc604feb474552bf099ec19e5774d3
Source dataset
uspto-grants-2001_10
Patent number
US06297246B1

Reaction notes

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