Morpholine → HCID 57830135, compound

HRID 2114075Notes

Reaction equation

HRID 2114075 reaction equation
Br[C:2]1[C:10]2[C:5](=[N:6][CH:7]=[C:8]([C:11]3[CH:16]=[CH:15][C:14]([N:17]([CH3:19])[CH3:18])=[CH:13][CH:12]=3)[CH:9]=2)[N:4]([CH2:20][O:21][CH2:22][CH2:23][Si:24]([CH3:27])([CH3:26])[CH3:25])[CH:3]=1.[NH:28]1[CH2:33][CH2:32][O:31][CH2:30][CH2:29]1.O.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>CN(C)CCO.[Cl-].[Na+].O.[Cu]>[CH3:18][N:17]([CH3:19])[C:14]1[CH:15]=[CH:16][C:11]([C:8]2[CH:9]=[C:10]3[C:2]([N:28]4[CH2:33][CH2:32][O:31][CH2:30][CH2:29]4)=[CH:3][N:4]([CH2:20][O:21][CH2:22][CH2:23][Si:24]([CH3:27])([CH3:26])[CH3:25])[C:5]3=[N:6][CH:7]=2)=[CH:12][CH:13]=1

Participants

7

Reactant 3

HCID 8083MorpholineHCID 22031701Potassium phosphate, tribasic, monohydrateHCID 59812087HCID 59812087, compound

Product 1

HCID 57830135HCID 57830135, compoundYield 17.7%

Reagents, catalysts & solvents 3

HCID 23978CopperCatalystHCID 79022-(Dimethylamino)ethanolSolventHCID 57417360Sodium chloride; waterSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of 60 (0.055 g, 0.12 mmol), morpholine (0.021 mL, 0.24 mmol), tri-potassium phosphate monohydrate (0.057 g, 0.25 mmol), and copper (powder) (0.00078 g, 0.012 mmol) in N,N-dimethylethanolamine (1 mL) was heated at 120° C. for 2 days. The mixture was cooled and poured into brine and extracted with AcOEt. The organic layer was washed with brine twice, dried (MgSO4), concentrated, and purified by means of preparative TLC with hexane:AcOEt as eluent to afford 61 (0.0096 g, 17%) as a tan syrup. 1H NMR (400 MHz, CDCl3) δ 0.00 (s, 9H), 0.88-0.95 (m, 2H), 3.01 (s, 6H), 3.07-3.14 (m, 4H), 3.51-3.57 (m, 2H), 3.91-3.97 (m, 4H), 5.63 (s, 2H), 6.82-6.88 (m, 3H), 7.48-7.53 (m, 2H), 8.00 (d, J=0.21 Hz, 1H), 8.52 (d, J=0.21 Hz, 1H).

Workup

  1. temperatureThe mixture was cooled
  2. extractionextracted with AcOEt
  3. washThe organic layer was washed with brine twice
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated
  6. custompurified by means of preparative TLC with hexane

Sources & evidence

ORD record
ord-5c3f8e56b3e24437aedabd79154df957
Source dataset
uspto-grants-2008_10
Patent number
US07432375B2

Reaction notes

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