Morpholine → HCID 19913646, compound

HRID 1090664Notes

Reaction equation

HRID 1090664 reaction equation
[C:1]([C:6]1[CH:7]=[N:8][C:9]2[C:14]([C:15]=1[NH:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[CH3:23])=[CH:13][CH:12]=[CH:11][C:10]=2[CH:24]1[CH2:26][O:25]1)(=[O:5])[CH2:2][CH2:3][CH3:4].[NH:27]1[CH2:32][CH2:31][O:30][CH2:29][CH2:28]1>O1CCOCC1>[C:1]([C:6]1[CH:7]=[N:8][C:9]2[C:14]([C:15]=1[NH:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[CH3:23])=[CH:13][CH:12]=[CH:11][C:10]=2[CH:24]([OH:25])[CH2:26][N:27]1[CH2:32][CH2:31][O:30][CH2:29][CH2:28]1)(=[O:5])[CH2:2][CH2:3][CH3:4]

Participants

4

Reactant 2

HCID 8083MorpholineHCID 99749123-Butyryl-4-(2-methylphenylamino)-8oxiranylquinoline

Product 1

HCID 19913646HCID 19913646, compoundYield 47.1%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

3-Butyryl-4-(2-methylphenylamino)-8-oxiranylquinoline (1.0 g, 2.89 mmol) and morpholine (1.0 g, 11.55 mmol) in dioxan (20 ml) were heated under reflux for 9 hours. The dioxan was evaporated and the residue dissolved in ethyl acetate, washed with brine, dried and evaporated to an oil which crystallised from ether. Recrystallisation from dichloromethane/ether gave 3-butyryl-4-(2-methylphenylamino)-8-(1-hydroxy-2-morpholinoethyl)quinoline (0.59 g, 47%), m.p. 135°-137°.

Workup

  1. temperatureunder reflux for 9 hours
  2. customThe dioxan was evaporated
  3. dissolutionthe residue dissolved in ethyl acetate
  4. washwashed with brine
  5. customdried
  6. customevaporated to an oil which
  7. customcrystallised from ether
  8. customRecrystallisation from dichloromethane/ether

Sources & evidence

ORD record
ord-36092fa0cd0b4b538eba1e2c7baa52c5
Source dataset
uspto-grants-1992_01
Patent number
US05082841

Reaction notes

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