Hexane → 2-(2-Methylphenyl)-3-morpholinoimidazo[2,1-a]isoquinoline

HRID 376326Notes

Reaction equation

HRID 376326 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.Cl[CH2:31][CH2:32][O:33][CH2:34][CH2:35]Cl>CN(C)C=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[N:1]1[CH2:35][CH2:34][O:33][CH2:32][CH2:31]1

Participants

6

Reactant 4

HCID 8058HexaneHCID 8115Bis(2-chloroethyl) etherHCID 24758Sodium hydrideHCID 15462240HCID 15462240, compound2×

Product 1

HCID 154625772-(2-Methylphenyl)-3-morpholinoimidazo[2,1-a]isoquinolineYield 28.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A solution of 5.5 g of 3-amino-2-(2-methylphenyl)imidazo[2,1-a]isoquinoline (Compound 3) in 50 ml of dry N,N-dimethylformamide was added dropwise to a solution of 1.8 g of sodium hydride in oil (prewashed with hexane) in 150 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, 3.2 g of bis(2-chloroethyl)ether was added dropwise. The mixture was stirred at room temperature for 2 hours, and then at 60° C. for 2 hours. The reaction mixture was poured into ice 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 to give 2.0 g of 2-(2-methylphenyl)-3-morpholinoimidazo[2,1-a]isoquinoline (Compound 218) as a yellow oily material. To a solution of 2.0 g of the product in 80 ml of ether was added a saturated solution of hydrogen chloride in ether. Precipitated crystalline was collected by filtration, and washed with ethanol to give 1.1 g of the title compound as a yellowish white powder.

Workup

  1. stirringThe mixture was stirred at room temperature for 2 hours
  2. waitat 60° C. for 2 hours
  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

Sources & evidence

ORD record
ord-f58bd10922aa4b43b222bc84a2eef335
Source dataset
uspto-grants-2000_02
Patent number
US06020342

Reaction notes

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