Morpholine → Ammonia

HRID 1988887Notes

Reaction equation

HRID 1988887 reaction equation
[Br:1][C:2]1[CH:11]=[CH:10][C:5]2[C:6](=O)[NH:7][O:8][C:4]=2[CH:3]=1.S(OS(C(F)(F)F)(=O)=O)(C(F)(F)F)(=O)=O.[NH:27]1[CH2:32][CH2:31][O:30][CH2:29][CH2:28]1.C(N(C(C)C)CC)(C)C>ClCCl.C1CCCCC1.C(#N)C.N1C=CC=CC=1>[NH3:7].[Br:1][C:2]1[CH:11]=[CH:10][C:5]2[C:6]([N:27]3[CH2:32][CH2:31][O:30][CH2:29][CH2:28]3)=[N:7][O:8][C:4]=2[CH:3]=1

Participants

10

Reactant 4

HCID 8083MorpholineHCID 67749Trifluoromethanesulfonic anhydrideHCID 81531DiisopropylethylamineHCID 112296276-bromo-1,2-benzisoxazol-3-ol2×

Product 2

HCID 222AmmoniaHCID 591273816-Bromo-3-(4-morpholinyl)-1,2-benzisoxazole

Reagents, catalysts & solvents 4

HCID 1049PyridineSolventHCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolventHCID 8078CyclohexaneSolvent

Procedure

An ice-bath cooled solution of 6-bromo-1,2-benzisoxazol-3 (2H)-one (Intermediate 24) (0.15 g) and dry pyridine (0.15 ml) in dry dichloromethane (12 ml) was stirred under nitrogen and treated with triflic anhydride (180 μL). The solution was stirred at room temp. for 90 min, diluted with cyclohexane then applied to a Varian Bond-Elut SPE cartridge (silica, 5 g) and eluted with cyclohexane and dichloromethane to give a colourless oil. The oil was dissolved in acetonitrile (4 ml) treated with morpholine (61 μL) and diisopropylethylamine (0.15 ml) then stirred at 70° under nitrogen for 16 h. The cooled reaction mixture was purified on a Varian Bond-Elut SPE cartridge (silica, 5 g) using dichloromethane:ethanol:0.88 ammonia to give the title compound as a white solid (0.03 g).

Workup

  1. stirringThe solution was stirred at room temp. for 90 min
  2. washeluted with cyclohexane and dichloromethane
  3. customto give a colourless oil
  4. stirringthen stirred at 70° under nitrogen for 16 h
  5. customThe cooled reaction mixture
  6. customwas purified on a Varian Bond-Elut SPE cartridge (silica, 5 g)

Sources & evidence

ORD record
ord-3301ce729ef74b4f834a933f9cec8204
Source dataset
uspto-grants-2010_01
Patent number
US07642276B2

Reaction notes

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