4-Piperidinecarboxylic acid → 5-Bromo-2-(piperidin-4-yl)benzo[d]oxazole

HRID 710074Notes

Reaction equation

HRID 710074 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([Br: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-].[Na+].CCOC(C)=O.O>O>[Br:8][C:6]1[CH:5]=[CH:4][C:3]2[O:9][C:16]([CH:13]3[CH2:14][CH2:15][NH:10][CH2:11][CH2:12]3)=[N:1][C:2]=2[CH:7]=1

Participants

6

Reactant 4

HCID 37734-Piperidinecarboxylic acidHCID 14798Sodium HydroxideHCID 3518402-Amino-4-BromophenolHCID 22728543Water ethylacetate

Product 1

HCID 711141905-Bromo-2-(piperidin-4-yl)benzo[d]oxazoleYield 49.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
190 °C

Procedure

2-amino-4-bromophenol (1.2 g, 5.8 mmol) and piperidine-4-carboxylic acid (0.74 g, 5.8 mmol) were dissolved in polyphosphoric acid (30 g). This mixture was heated at 190° C. for three and half hours. Reaction mixture cooled to rt and diluted with water (100 ml). Aqueous layer basified with sodium hydroxide pellets to pH 9. Work up (AcOEt/H2O) followed removal of AcOEt afforded the titled compound (0.8 g) as a pale-yellow gummy solid.

Workup

  1. customReaction mixture
  2. temperaturecooled to rt
  3. customremoval of AcOEt

Sources & evidence

ORD record
ord-4bd52488b0da4976ad08ebc837cf304a
Source dataset
uspto-grants-2015_11
Patent number
US09181214B2

Reaction notes

Loading…