Isopropyl iodide → 4-(4-Isopropyl-3,5-dimethylpiperazin-1-yl)benzaldehyde

HRID 591658Notes

Reaction equation

HRID 591658 reaction equation
[CH3:1][CH:2]1[NH:7][CH:6]([CH3:8])[CH2:5][N:4]([C:9]2[CH:16]=[CH:15][C:12]([CH:13]=[O:14])=[CH:11][CH:10]=2)[CH2:3]1.C([O-])([O-])=O.[K+].[K+].I[CH:24]([CH3:26])[CH3:25]>CC#N>[CH:24]([N:7]1[CH:2]([CH3:1])[CH2:3][N:4]([C:9]2[CH:16]=[CH:15][C:12]([CH:13]=[O:14])=[CH:11][CH:10]=2)[CH2:5][CH:6]1[CH3:8])([CH3:26])[CH3:25]

Participants

5

Reactant 3

HCID 6362Isopropyl iodide2×HCID 11430Potassium Carbonate2×HCID 866620204-(3,5-Dimethylpiperazin-1-yl)benzaldehyde

Product 1

HCID 866620244-(4-Isopropyl-3,5-dimethylpiperazin-1-yl)benzaldehydeYield 46%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a mixture of 4-(3,5-dimethylpiperazin-1-yl)benzaldehyde (1.0 g, 4.6 mmol) and K2CO3 (1.3 g, 9.2 mmol) in CH3CN (10 mL) was added 2-iodopropane (2.3 mL, 22.9 mmol) and the reaction was stirred at reflux temperature overnight. Additional 2-iodopropane (2.3 mL, 22.9 mmol) and K2CO3 (1.3 g, 9.2 mmol) were added and the reaction was continued to reflux overnight. The mixture was concentrated in vacuo and purified by flash chromatography on silica gel, eluting with 1% to 10% MeOH/CH2Cl2, to afford 4-(4-isopropyl-3,5-dimethylpiperazin-1-yl)benzaldehyde (0.550 g, 46%).

Workup

  1. temperatureat reflux temperature overnight
  2. temperatureto reflux overnight
  3. concentrationThe mixture was concentrated in vacuo
  4. custompurified by flash chromatography on silica gel
  5. washeluting with 1% to 10% MeOH/CH2Cl2

Sources & evidence

ORD record
ord-d3ee319918d14fa3962fcdbaa5613116
Source dataset
uspto-grants-2016_01
Patent number
US09238640B2

Reaction notes

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