Water → 6-morpholino-3,4-dihydronaphthalen-1(2H)-one

HRID 1362746Notes

Reaction equation

HRID 1362746 reaction equation
FC(F)(F)S(O[C:7]1[CH:16]=[CH:15][C:14]2[C:13](=[O:17])[CH2:12][CH2:11][CH2:10][C:9]=2[CH:8]=1)(=O)=O.[NH:20]1[CH2:25][CH2:24][O:23][CH2:22][CH2:21]1.P([O-])([O-])([O-])=O.[K+].[K+].[K+].O>COCCOC.[Pd].[Pd].C(=CC(C=CC1C=CC=CC=1)=O)C1C=CC=CC=1.C(=CC(C=CC1C=CC=CC=1)=O)C1C=CC=CC=1.C(=CC(C=CC1C=CC=CC=1)=O)C1C=CC=CC=1.C(P(C(C)(C)C)C1C=CC=CC=1C1C=CC=CC=1)(C)(C)C.C(OCC)(=O)C>[N:20]1([C:7]2[CH:8]=[C:9]3[C:14](=[CH:15][CH:16]=2)[C:13](=[O:17])[CH2:12][CH2:11][CH2:10]3)[CH2:25][CH2:24][O:23][CH2:22][CH2:21]1

Participants

9

Reactant 4

HCID 962WaterHCID 8083MorpholineHCID 62657Potassium Phosphate, TribasicHCID 110983845-Oxo-5,6,7,8-tetrahydronaphthalen-2-yl trifluoromethanesulfonate

Product 1

HCID 131795016-morpholino-3,4-dihydronaphthalen-1(2H)-oneYield 95.8%

Reagents, catalysts & solvents 4

HCID 27342152-(Di-tert-butylphosphino)biphenylCatalystHCID 9832798Tris(dibenzylideneacetone) dipalladiumCatalystHCID 80711,2-DimethoxyethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 5-oxo-5,6,7,8-tetrahydronaphthalen-2-yl trifluoromethanesulfonate (3.40 g), morpholine (5.18 g), tripotassium phosphate (3.79 g), tris(dibenzylideneacetone) dipalladium (0) (109 mg) and 2-(di-tert-butylphosphino)biphenyl (71 mg) in 1,2-dimethoxyethane (24 mL) was stirred in a nitrogen atmosphere at 80° C. for one and a half hours. The reaction solution was returned to room temperature, and water and ethyl acetate were added to the reaction solution and the organic layer was partitioned. The organic layer was washed with brine, and then dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The resulting residue was purified by silica gel chromatography (elution solvent: heptane-ethyl acetate system) to obtain 2.56 g of the title compound. Properties data of the compound are as follows.

Workup

  1. customwas returned to room temperature
  2. customthe organic layer was partitioned
  3. washThe organic layer was washed with brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe resulting residue was purified by silica gel chromatography (elution solvent: heptane-ethyl acetate system)

Sources & evidence

ORD record
ord-6ea7c1d79b4a4b2cbad4d0f01e5846c5
Source dataset
uspto-grants-2011_02
Patent number
US07880009B2

Reaction notes

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