Morpholine → HCID 21412369, compound

HRID 2071761Notes

Reaction equation

HRID 2071761 reaction equation
[NH:1]1[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.[Cl:7][C:8]1[N:17]=[C:16]([NH:18][CH2:19][CH2:20][N:21]([CH2:24][CH3:25])[CH2:22][CH3:23])[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[N:9]=1>O1CCCC1>[ClH:7].[O:4]1[CH2:5][CH2:6][N:1]([C:8]2[N:17]=[C:16]([NH:18][CH2:19][CH2:20][N:21]([CH2:24][CH3:25])[CH2:22][CH3:23])[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[N:9]=2)[CH2:2][CH2:3]1

Participants

4

Reactant 2

HCID 8083MorpholineHCID 12703171HCID 12703171, compound

Product 1

HCID 21412369HCID 21412369, compoundYield 41.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 5 g of morpholine in 50 ml of tetrahydrofuran was added to 6.8 g of 2-chloro-4-(2-diethylaminoethylamino)quinazoline in 50 ml of tetrahydrofuran. The reaction mixture was heated at reflux overnight and then evaporated to dryness. The residue was suspended in dilute sodium hydroxide solution and the crude product was extracted into ether. The ether extract was washed with water, dried over anhydrous sodium sulfate, filtered, and the filtrate evaporated to dryness. Attempts to crystallize the residue were unsuccessful. The residue then was distilled under reduced pressure. The distillate was dissolved in ether and treated with hydrogen chloride. The product was collected by filtration and dried, giving 3.7 g of 2-morpholino-4-(2-diethylaminoethylamino)quinazoline hydrochloride; m.p. 216°-220°. The following elemental analysis was obtained:

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux overnight
  3. customevaporated to dryness
  4. extractionthe crude product was extracted into ether
  5. extractionThe ether extract
  6. washwas washed with water
  7. dry with materialdried over anhydrous sodium sulfate
  8. filtrationfiltered
  9. customthe filtrate evaporated to dryness
  10. customto crystallize the residue
  11. distillationThe residue then was distilled under reduced pressure
  12. dissolutionThe distillate was dissolved in ether
  13. additiontreated with hydrogen chloride
  14. filtrationThe product was collected by filtration
  15. customdried

Sources & evidence

ORD record
ord-f1413379479942c6b933e210707977df
Source dataset
uspto-grants-1977_09
Patent number
US04048312

Reaction notes

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