Piperidine → HCID 54180801, compound

HRID 1815376Notes

Reaction equation

HRID 1815376 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].[C:14]([C:17]1[CH:18]=[C:19]2[C:23](=[CH:24][CH:25]=1)[NH:22][C:21](=[O:26])[CH2:20]2)([OH:16])=[O:15].N1CCCCC1>C(O)C>[C:1]([CH2:4][CH2:5][C:6]1[C:7]([CH3:13])=[C:8]([CH:11]=[C:20]2[C:19]3[C:23](=[CH:24][CH:25]=[C:17]([C:14]([OH:16])=[O:15])[CH:18]=3)[NH:22][C:21]2=[O:26])[NH:9][CH:10]=1)([OH:3])=[O:2]

Participants

5

Reactant 3

HCID 8082PiperidineHCID 27733182-Oxindole-5-carboxylic acidHCID 151607523-(5-formyl-4-methyl-1H-pyrrol-3-yl)propanoic acid

Product 1

HCID 54180801HCID 54180801, compoundYield 30%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

4-(2-Carboxyethyl)-2-formyl-3-methylpyrrole (90.6 mg), 88.6 mg 5-carboxy-2-oxindole, and 75 μL piperidine in 2 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. The crude product was purified by chromatography on a silica gel column using ethyl acetate-hexane-acetic acid as the eluant to give 51 mg(30%) of the title compound as a yellow 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
  6. customThe crude product was purified by chromatography on a silica gel column

Sources & evidence

ORD record
ord-b61f65e7af814117bfbed60df2c6609f
Source dataset
uspto-grants-2005_04
Patent number
US06878733B1

Reaction notes

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