Ammonia → HCID 135621704, compound

HRID 64864Notes

Reaction equation

HRID 64864 reaction equation
Cl[C:2]1[NH:11][CH2:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][C:8]=2[N:12]2[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]2)[N:3]=1.Br[CH2:19][C:20]([O:22]CC)=O.[OH-].[Na+].[NH3:27]>C(Cl)Cl.[I-].C([N+](CCCC)(CCCC)CCCC)CCC>[N:12]1([C:8]2[CH:7]=[CH:6][CH:5]=[C:4]3[C:9]=2[CH2:10][N:11]2[CH2:19][C:20](=[O:22])[NH:27][C:2]2=[N:3]3)[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1

Participants

7

Reactant 4

HCID 222AmmoniaHCID 7748Ethyl bromoacetateHCID 14798Sodium HydroxideHCID 178478311HCID 178478311, compound

Product 1

HCID 135621704HCID 135621704, compound

Reagents, catalysts & solvents 2

HCID 67553Tetrabutylammonium IodideCatalystHCID 6344DichloromethaneSolvent

Procedure

1.9 g of 2-chloro-5-piperidino-3,4-dihydroquinazoline was dissolved in 50 ml of methylene chloride. 1.4 g of ethyl bromoacetate and 0.2 g of tetrabutylammonium iodide were added to the solution, and 7.5 ml of a 10N sodium hydroxide aqueous solution was further added thereto in a nitrogen stream while stirring. After stirring at room temperature for 1 hour, the reaction mixture was washed with water, dried, and distilled off under reduced pressure to obtain crude oily ethyl (2-chloro-5-piperidino-3,4-dihydroquinazolin-3-yl)acetate in a substantially quantitative yield. The crude product was added to 10 ml of a 10% ethanolic solution of ammonia and heated in a sealed tube at 120° to 130° C. for 4 hours. After cooling, crystals thus precipitated were collected by filtration, washed with water and dried to obtain 0.65 g of 6-piperidino-1,2,3,5-tetrahydroimidazo[2,1-b]quinazolin-2-one. This product was suspended in methanol and dissolved therein by adjusting the pH to 1 to 2 with concentrated hydrochloric acid. The solution was treated with activated carbon, followed by filtration. The filtrate was concentrated under reduced pressure, and the crystals thus precipitated were collected to obtain a hydrochloride (melting point: 242°-245° C. with decomposition).

Workup

  1. additionwas further added
  2. stirringAfter stirring at room temperature for 1 hour
  3. washthe reaction mixture was washed with water
  4. customdried
  5. distillationdistilled off under reduced pressure
  6. customto obtain crude oily ethyl (2-chloro-5-piperidino-3,4-dihydroquinazolin-3-yl)acetate in a substantially quantitative yield
  7. temperatureheated in a sealed tube at 120° to 130° C. for 4 hours
  8. temperatureAfter cooling
  9. customcrystals thus precipitated
  10. filtrationwere collected by filtration
  11. washwashed with water
  12. customdried

Sources & evidence

ORD record
ord-ad51e041879740bebfcc916722b5ddc5
Source dataset
uspto-grants-1986_09
Patent number
US04610987

Reaction notes

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