Piperazine → 1-Phenyl-2-piperazin-1-yl-1H-indole-3-carboxaldehyde

HRID 751335Notes

Reaction equation

HRID 751335 reaction equation
Cl[C:2]1[N:3]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[C:4]2[C:9]([C:10]=1[CH:11]=[O:12])=[CH:8][CH:7]=[CH:6][CH:5]=2.[NH:19]1[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]1.O1CCOCC1>O>[N:19]1([C:2]2[N:3]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[C:4]3[C:9]([C:10]=2[CH:11]=[O:12])=[CH:8][CH:7]=[CH:6][CH:5]=3)[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]1

Participants

5

Reactant 3

HCID 4837PiperazineHCID 312751,4-DioxaneHCID 3147932-chloro-1-phenyl-1H-indole-3-carbaldehyde

Product 1

HCID 539968311-Phenyl-2-piperazin-1-yl-1H-indole-3-carboxaldehydeYield 36.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 2-chloro-1-phenyl-1H-indole-3-carboxaldehyde (2.0 g, 7.83 mmol), piperazine (6.73 g, 78.3 mmol) and dioxane (25 mL) is heated at reflux overnight. After cooling to room temperature, water (100 mL) is added and after 1 hr the solids are collected by filtration, washed with water and purified by flash chromatography eluting with chloroform-5% methanol. Product containing fractions are combined and concentrated to afford 2-(piperazin-1-yl)-1-phenyl-1H-indol-3-carboxaldehyde (0.87 g, 36%) as a beige solid. A sample, mp 175° C., is purified by flash chromatography eluting with dichloromethane-5% methanol. NMR (CDCl3) 10.29 (1H, s), 8.27 (1H, d), 7.60 (2H, m), 7.51 (1H, t), 7.40 (2H, d), 7.23 (1H, m), 7.15 (1H, t), 6.98 (1H, d), 3.27 (4H, m), 2.78 (4H, m).

Workup

  1. temperatureis heated
  2. temperatureat reflux overnight
  3. filtrationare collected by filtration
  4. washwashed with water
  5. custompurified by flash chromatography
  6. washeluting with chloroform-5% methanol
  7. additionProduct containing fractions
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-ee8c8708665149d9a7491743af31ede7
Source dataset
uspto-grants-2008_07
Patent number
US07405300B2

Reaction notes

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