Ethanol → HCID 21412356, compound

HRID 1076365Notes

Reaction equation

HRID 1076365 reaction equation
[Cl:1][C:2]1[N:11]=[C:10]([N:12]2[CH2:17][CH2:16][N:15]([CH3:18])[CH2:14][CH2:13]2)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1.[NH:19]1[CH2:24][CH2:23][O:22][CH2:21][CH2:20]1.C(O)C.[OH-].[Na+]>O>[ClH:1].[ClH:1].[O:22]1[CH2:23][CH2:24][N:19]([C:2]2[N:11]=[C:10]([N:12]3[CH2:17][CH2:16][N:15]([CH3:18])[CH2:14][CH2:13]3)[C:9]3[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=3)[N:3]=2)[CH2:20][CH2:21]1

Participants

6

Reactant 4

HCID 702EthanolHCID 8083MorpholineHCID 14798Sodium HydroxideHCID 214123752-Chloro-4-(4-methyl-1-piperazinyl)quinazoline

Product 1

HCID 21412356HCID 21412356, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 5 g of 2-chloro-4-(4-methylpiperazinyl)quinazoline, 5 ml of morpholine, and 10 ml of ethanol was refluxed for 16 hours. The reaction mixture was diluted with 200 ml of water, made alkaline with 10 ml of 50 percent aqueous sodium hydroxide solution, and extracted with ether. The ether extract was washed with water, dried over anhydrous sodium sulfate, filtered, and evaporated to dryness. The residue was dissolved in 500 ml of ether. The ethereal solution was treated with excess hydrogen chloride and the resulting precipitate was collected by filtration. The crude product was recrystallized twice from 95 percent ethanol, giving 3 g of 2-morpholino-4-(4-methylpiperazinyl)quinazoline dihydrochloride, dihydrate; m.p. 310°-312° with decomposition. The following analytical data were obtained:

Workup

  1. temperaturewas refluxed for 16 hours
  2. extractionextracted with ether
  3. extractionThe ether extract
  4. washwas washed with water
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. customevaporated to dryness
  8. dissolutionThe residue was dissolved in 500 ml of ether
  9. additionThe ethereal solution was treated with excess hydrogen chloride
  10. filtrationthe resulting precipitate was collected by filtration
  11. customThe crude product was recrystallized twice from 95 percent ethanol

Sources & evidence

ORD record
ord-4831b6de1bbc48ab9d2cef4f7091340b
Source dataset
uspto-grants-1976_05
Patent number
US03956495

Reaction notes

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