Piperidine → HCID 54504632, compound

HRID 1243461Notes

Reaction equation

HRID 1243461 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].[OH:15][C:16]1[CH:24]=[C:23]2[C:19]([CH2:20][C:21](=[O:25])[NH:22]2)=[CH:18][CH:17]=1.N1CCCCC1>C(O)C>[OH:15][C:16]1[CH:24]=[C:23]2[C:19]([C:20](=[CH:12][C:9]3[NH:8][C:7]([CH3:14])=[C:6]([CH2:5][CH2:4][C:1]([OH:3])=[O:2])[C:10]=3[CH3:11])[C:21](=[O:25])[NH:22]2)=[CH:18][CH:17]=1

Participants

5

Reactant 3

HCID 8082PiperidineHCID 15125203-(5-formyl-2,4-dimethyl-1H-pyrrol-3-yl)propanoic AcidHCID 27841396-hydroxy-2,3-dihydro-1H-indol-2-one

Product 1

HCID 54504632HCID 54504632, compoundYield 40.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

3-(2-carboxyethyl)-2,4-dimethyl-5-formylpyrrole (82 mg), 63 mg 6-hydroxy-2-oxindole, and 48 μL piperidine in 2 mL of ethanol were heated at 90° C. for two days. The reaction mixture was cooled, concentrated, and purified by silica gel column chromotography eluting with ethyl acetate-hexane-acetic acid to give 55 mg (40%) of the title compound as an dark brown solid.

Workup

  1. temperatureThe reaction mixture was cooled
  2. concentrationconcentrated
  3. custompurified by silica gel column chromotography
  4. washeluting with ethyl acetate-hexane-acetic acid

Sources & evidence

ORD record
ord-3839827ba059425dbe5bd1d3bff17c35
Source dataset
uspto-grants-2006_10
Patent number
US07119090B2

Reaction notes

Loading…