4-Piperidinecarboxylic acid → HCID 71089609, compound

HRID 710076Notes

Reaction equation

HRID 710076 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([Br:8])=[CH:4][C:3]=1[OH:9].[NH:10]1[CH2:18][CH2:17][CH:13]([C:14](O)=O)[CH2:12][CH2:11]1.[OH-].[Na+]>CCOC(C)=O.O>[Br:8][C:5]1[CH:6]=[CH:7][C:2]2[N:1]=[C:14]([CH:13]3[CH2:17][CH2:18][NH:10][CH2:11][CH2:12]3)[O:9][C:3]=2[CH:4]=1

Participants

5

Reactant 3

HCID 37734-Piperidinecarboxylic acidHCID 14798Sodium HydroxideHCID 143206052-Amino-5-bromophenol

Product 1

HCID 71089609HCID 71089609, compoundYield 25.8%

Reagents, catalysts & solvents 1

HCID 22728543Water ethylacetateSolvent

Conditions

Temperature
190 °C

Procedure

2-amino-5-bromophenol (1.3 g, 6.9 mmol) and isonipecotic acid (893 mg, 6.91 mmol) were dissolved in polyphosphoric acid (39 g). This mixture was heated to 190° C. for 3 h. After 3 h, reaction mixture cooled to rt and basified with 10% aqueous NaOH solution to pH 8. Work up (EtOAc/H2O) followed by removal of EtOAc afforded the title compound (500 mg) as a black solid. It was used in the next step without further purification.

Workup

  1. customreaction mixture
  2. temperaturecooled to rt
  3. customfollowed by removal of EtOAc

Sources & evidence

ORD record
ord-31ac17804c3d44209d3b7cdde9742aa4
Source dataset
uspto-grants-2015_11
Patent number
US09181214B2

Reaction notes

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