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

HRID 2291185
Notes
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Reaction equation

HRID 2291185 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
ParticipantsProcedureWorkupSources & evidenceReaction notes

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-d99857dc294642e48e5cb0d10df12c2d
Source dataset
uspto-grants-1986_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04619932

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes