Hexane → 2-(2-Methylphenyl)-3-[(1-phenylethyl)amino]imidazo[2,1-a]isoquinoline

HRID 376324Notes

Reaction equation

HRID 376324 reaction equation
[NH2:1][C:2]1[N:6]2[CH:7]=[CH:8][C:9]3[C:14]([C:5]2=[N:4][C:3]=1[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[CH3:21])=[CH:13][CH:12]=[CH:11][CH:10]=3.[H-].[Na+].CCCCCC.Br[CH:31]([C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)[CH3:32]>CN(C)C=O.O>[CH3:21][C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=1[C:3]1[N:4]=[C:5]2[C:14]3[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=3)[CH:8]=[CH:7][N:6]2[C:2]=1[NH:1][CH:31]([C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)[CH3:32]

Participants

7

Reactant 4

HCID 8058HexaneHCID 11454(1-Bromoethyl)benzeneHCID 24758Sodium hydrideHCID 15462240HCID 15462240, compound2×

Product 1

HCID 154625712-(2-Methylphenyl)-3-[(1-phenylethyl)amino]imidazo[2,1-a]isoquinolineYield 76.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent3×

Procedure

A solution of 5 g of 3-amino-2-(2-methylphenyl)imidazo[2,1-a]isoquinoline (Compound 3) in 30 ml of dry N,N-dimethylformamide was added dropwise to a solution of 1.2 g of sodium hydride in oil (prewashed with hexane) in 10 ml of dry N,N-dimethylformamide over 30 minutes under dry argon atmosphere at room temperature. After the mixture was stirred for further 1 hour, a solution of 4.1 g of (1-bromoethyl)benzene in 30 ml of dry N,N-dimethylformamide was added dropwise. When addition was complete, the mixture was stirred at room temperature for 1 hour. The solution was poured into water and extracted with ethyl acetate. The extract was washed with water and saturated saline, and dried over anhydrous magnesium sulfate. The drying agent was removed by filtration, and the solvent was removed under reduced pressure. The residue was purified by column chromatography on silica gel, and recrystallized from benzene/hexane to give 5.3 g of the title compound as colorless needles.

Workup

  1. additionWhen addition
  2. stirringthe mixture was stirred at room temperature for 1 hour
  3. extractionextracted with ethyl acetate
  4. washThe extract was washed with water and saturated saline
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customThe drying agent was removed by filtration
  7. customthe solvent was removed under reduced pressure
  8. customThe residue was purified by column chromatography on silica gel
  9. customrecrystallized from benzene/hexane

Sources & evidence

ORD record
ord-9da47e4211f24800af47903f25ad6dc0
Source dataset
uspto-grants-2000_02
Patent number
US06020342

Reaction notes

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