Morpholine → HCID 23121824, compound

HRID 1713532Notes

Reaction equation

HRID 1713532 reaction equation
[C:1]1([C:7]2([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[CH:11]3[CH2:12][NH:13][CH2:14][CH2:15][N:10]3[C:9](=[O:16])[O:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Br[CH2:24][CH2:25][N:26]=[C:27]=[O:28].[NH:29]1[CH2:34][CH2:33][O:32][CH2:31][CH2:30]1>C1(C)C=CC=CC=1>[N:29]1([CH2:24][CH2:25][NH:26][C:27]([N:13]2[CH2:14][CH2:15][N:10]3[C:9](=[O:16])[O:8][C:7]([C:1]4[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=4)([C:17]4[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=4)[CH:11]3[CH2:12]2)=[O:28])[CH2:34][CH2:33][O:32][CH2:31][CH2:30]1

Participants

5

Reactant 3

HCID 8083MorpholineHCID 42559572-Bromoethyl isocyanateHCID 231218811,1-Diphenyltetrahydro-1H-oxazolo[3,4-a]pyrazin-3(5H)-one

Product 1

HCID 23121824HCID 23121824, compoundYield 26%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Hexahydro-1,1-diphenyl-3H-oxazolo[3,4-a]pyrazin-3-one (0.17 g, 0.58 mmol) was dissolved in toluene (1.5 mL). 2-Bromoethyl isocyanate (0.10 g, 0.67 mmol) was added thereto, and the mixture was stirred at room temperature for 2 hours. The reaction solution was concentrated under reduced pressure. The residue was subjected to silica gel column chromatography (ethyl acetate), and the fractions were collected and concentrated. The residue was dissolved in N,N-dimethylformamide (2 mL), morpholine (0.20 g, 3.9 mmol) was added thereto, and the mixture was stirred at 60° C. for 16 hours. To the reaction solution was added ice water, and the mixture was extracted with ethyl acetate. The organic layer was washed with water and concentrated under reduced pressure. The residue was purified with amino silica gel column chromatography (ethyl acetate), and crystallized from hexane to obtain the title compound (66 mg, yield 26%).

Workup

  1. concentrationThe reaction solution was concentrated under reduced pressure
  2. customthe fractions were collected
  3. concentrationconcentrated
  4. dissolutionThe residue was dissolved in N,N-dimethylformamide (2 mL)
  5. stirringthe mixture was stirred at 60° C. for 16 hours
  6. extractionthe mixture was extracted with ethyl acetate
  7. washThe organic layer was washed with water
  8. concentrationconcentrated under reduced pressure
  9. customThe residue was purified with amino silica gel column chromatography (ethyl acetate)
  10. customcrystallized from hexane

Sources & evidence

ORD record
ord-b8ac4ceb7e584ee4b4ecedbd1854f97a
Source dataset
uspto-grants-2010_09
Patent number
US07795267B2

Reaction notes

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