Morpholine → HCID 68578670, compound

HRID 886893Notes

Reaction equation

HRID 886893 reaction equation
Br[C:2]1[C:7]2[CH2:8][N:9]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:10][CH2:11][O:12][C:6]=2[CH:5]=[CH:4][CH:3]=1.[NH:20]1[CH2:25][CH2:24][O:23][CH2:22][CH2:21]1.CC(C)([O-])C.[Na+].O1CCOCC1>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].CC(C1C=C(C(C)C)C(C2C=CC=CC=2P(C2CCCCC2)C2CCCCC2)=C(C(C)C)C=1)C.O>[N:20]1([C:2]2[C:7]3[CH2:8][N:9]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:10][CH2:11][O:12][C:6]=3[CH:5]=[CH:4][CH:3]=2)[CH2:25][CH2:24][O:23][CH2:22][CH2:21]1

Participants

8

Reactant 4

HCID 8083MorpholineHCID 312751,4-DioxaneHCID 23676156Sodium t-butoxideHCID 68578195HCID 68578195, compound

Product 1

HCID 68578670HCID 68578670, compoundYield 78.5%

Reagents, catalysts & solvents 3

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 111557942-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenylCatalystHCID 962WaterSolvent

Procedure

A solution of tert-butyl 6-bromo-2,3-dihydro-1,4-benzoxazepine-4(5H)-carboxylate (150 mg, 0.457 mmol), morpholine (0.120 ml, 1.37 mmol), X-phos (13.0 mg, 0.0274 mmol), tris(dibenzylideneacetone)dipalladium(0) (82.4 mg, 0.00900 mmol), sodium tert-butoxide (65.8 mg, 0.684 mmol) and dioxane (3 ml) was stirred under an argon atmosphere for 2 hr at 80° C. The reaction mixture was poured into water, and the mixture was extracted with ethyl acetate. The extract was washed with water and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=2:1) to give the desired product (120 mg, 78.4%) as an oil.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe extract was washed with water
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=2:1)

Sources & evidence

ORD record
ord-fb64dbd1aaa74db38267dd1f65f65dd0
Source dataset
uspto-grants-2012_08
Patent number
US08247403B2

Reaction notes

Loading…