Diethyl Ether → 6-(1-Oxo-2-morpholinoethyl)-3,4-dihydrocarbostyril monohydrochloride

HRID 1462545Notes

Reaction equation

HRID 1462545 reaction equation
[O:1]=[C:2]([C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][CH:14]=1)[NH:11][C:10](=[O:15])[CH2:9][CH2:8]2)[CH2:3][Cl:4].[NH:16]1[CH2:21][CH2:20][O:19][CH2:18][CH2:17]1.CCOCC>O1CCOCC1>[ClH:4].[O:1]=[C:2]([C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][CH:14]=1)[NH:11][C:10](=[O:15])[CH2:9][CH2:8]2)[CH2:3][N:16]1[CH2:21][CH2:20][O:19][CH2:18][CH2:17]1

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 8083MorpholineHCID 49617906-(2-Chloroacetyl)-1,2,3,4-tetrahydroquinolin-2-one

Product 1

HCID 202294546-(1-Oxo-2-morpholinoethyl)-3,4-dihydrocarbostyril monohydrochloride

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

5.0 Grams of 6-(1-oxo-2-chloroethyl)-3,4-dihydrocarbostyril and 6.0 g of morpholine were dispersed in 120 ml of dioxane and stirred at 60°-70° C. for 12 hours. The reaction mixture was concentrated under a reduced pressure. The residue thus obtained was stirred with ether and the insoluble matter was collected by filtration and washed with water. Then the insoluble matter was dissolved in 80 ml of methanol and 10 ml of concentrated hydrochloric acid by heating and the solution was concentrated under a reduced pressure to dryness. The residue thus obtained was recrystallized from methanol-ether twice and obtained 5.9 g of 6-(1-oxo-2-morpholinoethyl)-3,4-dihydrocarbostyril monohydrochloride in colorless powdery product.

Workup

  1. concentrationThe reaction mixture was concentrated under a reduced pressure
  2. customThe residue thus obtained
  3. filtrationthe insoluble matter was collected by filtration
  4. washwashed with water
  5. dissolutionThen the insoluble matter was dissolved in 80 ml of methanol
  6. temperature10 ml of concentrated hydrochloric acid by heating
  7. concentrationthe solution was concentrated under a reduced pressure to dryness
  8. customThe residue thus obtained
  9. customwas recrystallized from methanol-ether twice

Sources & evidence

ORD record
ord-6fc07453a9654d5fb11cec197b01f721
Source dataset
uspto-grants-1984_07
Patent number
US04460593

Reaction notes

Loading…