Piperidine → HCID 53735577, compound

HRID 1815391Notes

Reaction equation

HRID 1815391 reaction equation
[C:1]([CH2:4][CH2:5][C:6]1[C:10]([CH3:11])=[C:9]([CH:12]=O)[NH:8][C:7]=1[CH3:14])([OH:3])=[O:2].[Br:15][C:16]1[CH:17]=[C:18]2[C:22](=[CH:23][CH:24]=1)[NH:21][C:20](=[O:25])[CH2:19]2.N1CCCCC1>C(O)C>[Br:15][C:16]1[CH:17]=[C:18]2[C:22](=[CH:23][CH:24]=1)[NH:21][C:20](=[O:25])[C:19]2=[CH:12][C:9]1[NH:8][C:7]([CH3:14])=[C:6]([CH2:5][CH2:4][C:1]([OH:3])=[O:2])[C:10]=1[CH3:11]

Participants

5

Reactant 3

HCID 8082PiperidineHCID 6111935-Bromo-2-oxindoleHCID 15125203-(5-formyl-2,4-dimethyl-1H-pyrrol-3-yl)propanoic Acid

Product 1

HCID 53735577HCID 53735577, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

3-(2-Carboxyethyl)-2,4-dimethyl-5-formylpyrrole (97.5 mg), 106 mg 5-bromo-2-oxindole, and 75 μL piperidine in 3 mL of ethanol were heated at 95° C. for 5 hours. The reaction mixture was cooled and concentrated. The residue was suspended in 6 N aqueous hydrochloric acid. The precipitate was filtered, washed with water to pH 6 and dried in a vacuum oven overnight to give 171 mg (88%) of the title compound as an orange solid.

Workup

  1. temperatureThe reaction mixture was cooled
  2. concentrationconcentrated
  3. filtrationThe precipitate was filtered
  4. washwashed with water to pH 6
  5. customdried in a vacuum oven overnight

Sources & evidence

ORD record
ord-50a2aa1368b545e9804a368c99a179b9
Source dataset
uspto-grants-2005_04
Patent number
US06878733B1

Reaction notes

Loading…