4-Piperidinecarboxylic acid → HCID 178419323, compound

HRID 710072Notes

Reaction equation

HRID 710072 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([NH2:9])[C:5]([NH2:8])=[CH:6][CH:7]=1.[NH:10]1[CH2:15][CH2:14][CH:13]([C:16](O)=O)[CH2:12][CH2:11]1.[OH-].[Na+]>O>[Br:1][C:2]1[CH:7]=[CH:6][C:5]2[NH:8][C:16]([CH:13]3[CH2:14][CH2:15][NH:10][CH2:11][CH2:12]3)=[N:9][C:4]=2[CH:3]=1

Participants

5

Reactant 3

HCID 37734-Piperidinecarboxylic acidHCID 14798Sodium HydroxideHCID 3235934-Bromobenzene-1,2-diamine

Product 1

HCID 178419323HCID 178419323, compoundYield 46.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
190 °C

Procedure

4-bromobenzene-1,2-diamine (1.43 g, 7.64 mmol) and piperidine-4-carboxylic acid (0.99 g, 7.64 mmol) were dissolved in polyphosphoric acid (20 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 14. Solid was filtered, washed with methanol and dried to obtain the title compound (1 g) as a dark brown solid.

Workup

  1. customReaction mixture
  2. temperaturecooled to rt
  3. filtrationSolid was filtered
  4. washwashed with methanol
  5. customdried

Sources & evidence

ORD record
ord-a0e93b4f597e4d079ac83733f4ace8d7
Source dataset
uspto-grants-2015_11
Patent number
US09181214B2

Reaction notes

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