Piperidine → HCID 54319103, compound

HRID 1937535Notes

Reaction equation

HRID 1937535 reaction equation
[C:1]([CH2:4][CH2:5][C:6]1[C:7]([CH3:13])=[C:8]([CH:11]=O)[NH:9][CH:10]=1)([OH:3])=[O:2].[Cl:14][C:15]1[CH:16]=[C:17]2[C:21](=[CH:22][CH:23]=1)[NH:20][C:19](=[O:24])[CH2:18]2.N1CCCCC1>C(O)C>[Cl:14][C:15]1[CH:16]=[C:17]2[C:21](=[CH:22][CH:23]=1)[NH:20][C:19](=[O:24])[C:18]2=[CH:11][C:8]1[NH:9][CH:10]=[C:6]([CH2:5][CH2:4][C:1]([OH:3])=[O:2])[C:7]=1[CH3:13]

Participants

5

Reactant 3

HCID 8082PiperidineHCID 1528015-ChlorooxindoleHCID 151607523-(5-formyl-4-methyl-1H-pyrrol-3-yl)propanoic acid

Product 1

HCID 54319103HCID 54319103, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

4-(2-Carboxyethyl)-2-formyl-3-methylpyrrole (4.5 g), 4.2 g of 5-chloro-2-oxindole, and 2.9 mL of piperidine in 50 mL of ethanol were heated to 95° C. for 5 hours. The reaction mixture was cooled and concentrated. The residue was suspended in acetone and the yellow precipitate was filtered, washed with cold ethanol, 2 N aqueous hydrochloric acid and water to pH 6 then dried in a vacuum oven overnight to give 7.2 g of the title compound (88%) as a yellow solid.

Workup

  1. temperatureThe reaction mixture was cooled
  2. concentrationconcentrated
  3. filtrationthe yellow precipitate was filtered
  4. washwashed with cold ethanol, 2 N aqueous hydrochloric acid and water to pH 6
  5. customthen dried in a vacuum oven overnight

Sources & evidence

ORD record
ord-6a5fa37ef75e433dbe92c51cc9b4833d
Source dataset
uspto-grants-2002_05
Patent number
US06395734B1

Reaction notes

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