Piperidine → HCID 66917516, compound

HRID 506870Notes

Reaction equation

HRID 506870 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][C:2]1=[O:10].[Br:11][C:12]1[CH:13]=[C:14]([CH:20]=O)[C:15]([O:18][CH3:19])=[N:16][CH:17]=1.N1CCCCC1>C(O)C>[Br:11][C:12]1[CH:13]=[C:14]([CH:20]=[C:3]2[C:4]3[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=3)[NH:1][C:2]2=[O:10])[C:15]([O:18][CH3:19])=[N:16][CH:17]=1

Participants

5

Reactant 3

HCID 8082PiperidineHCID 321710OxindoleHCID 15164035-Bromo-2-methoxypyridine-3-carbaldehyde

Product 1

HCID 66917516HCID 66917516, compoundYield 55.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of indolinone (130 mg, 0.98 mmol) in ethanol (5 mL) was added 5-bromo-2-methoxypyridine-3-carbaldehyde (J. Het. Chem, 1985, (22), 1583-1592) (200 mg, 0.98 mmol, 1 eq), followed by piperidine (0.194 mL, 1.9 mmol, 2 eq). The reaction mixture was heated at 80° C. for 2 hours and then allowed to cool to room temperature. The precipitate that formed was collected by filtration and washed with ethanol to give the title compound (180 mg, 55%).

Workup

  1. temperatureto cool to room temperature
  2. customThe precipitate that formed
  3. filtrationwas collected by filtration
  4. washwashed with ethanol

Sources & evidence

ORD record
ord-0ee0ad3c1fab443bba53b27ed98081dd
Source dataset
uspto-grants-2010_08
Patent number
US07786120B2

Reaction notes

Loading…