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

HRID 1739755Notes

Reaction equation

HRID 1739755 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[OH:8].[NH:9]1[CH2:17][CH2:16][CH:12]([C:13](O)=O)[CH2:11][CH2:10]1.[OH-].[Na+]>>[O:8]1[C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=2[N:1]=[C:13]1[CH:12]1[CH2:16][CH2:17][NH:9][CH2:10][CH2:11]1

Participants

4

Reactant 3

HCID 37734-Piperidinecarboxylic acidHCID 58012-AminophenolHCID 14798Sodium Hydroxide

Product 1

HCID 7704612-(Piperidin-4-yl)-1,3-benzoxazoleYield 12.2%

Procedure

A mixture of 2-aminophenol (20 g, 183 mmol), isonipecotic acid (23.7 g, 1 mol. equiv.) and polyphosphoric acid (50 ml) was heated together for 2 hours with stirring. The reaction mixture was cooled, poured onto ice (400 g) and solid sodium hydroxide (85 g) added until the solution achieved pH8. The solid was filtered off, slurried in water (500 ml) and filtered to give the title compound (4.5 g).

Workup

  1. temperaturewas heated together for 2 hours
  2. temperatureThe reaction mixture was cooled
  3. additionadded until the solution
  4. filtrationThe solid was filtered off
  5. filtrationfiltered

Sources & evidence

ORD record
ord-acd8afafd18a4f9cb44de7a5080b8798
Source dataset
uspto-grants-1999_10
Patent number
US05968923

Reaction notes

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