Acetophenone → HCID 67032701, compound

HRID 2167865Notes

Reaction equation

HRID 2167865 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][O:11][CH:10]([C:14]2[CH:19]=[CH:18][C:17](Br)=[CH:16][CH:15]=2)[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:21]([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)(=[O:23])[CH3:22].CC([O-])(C)C.[Na+].C1(P(C2C=CC=CC=2)C2C=CC3C(=CC=CC=3)C=2C2C3C(=CC=CC=3)C=CC=2P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C([O-])(O)=O.[Na+]>C1(C)C=CC=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.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[CH2:1]([N:8]1[CH2:13][CH2:12][O:11][CH:10]([C:14]2[CH:19]=[CH:18][C:17]([CH2:22][C:21]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)=[O:23])=[CH:16][CH:15]=2)[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

8

Reactant 5

HCID 7410AcetophenoneHCID 516892Sodium BicarbonateHCID 634876Binap, (A+-)-HCID 23676156Sodium t-butoxideHCID 580978794-Benzyl-2-(4-bromo-phenyl)-morpholine

Product 1

HCID 67032701HCID 67032701, compoundYield 47.8%

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 1140TolueneSolvent

Conditions

Temperature
110 °C

Procedure

To a degassed solution of 4-benzyl-2-(4-bromo-phenyl)-morpholine (205 mg; 0.62 mmol) and acetophenone (87 μL; 0.74 mmol) in toluene (4 mL) was added NaOtBu (148.3 mg; 1.54 mmol), 2,2′-bis(diphenylphosphino)-1,1′-binaphthyl (38.4 mg; 0.06 mmol) and tris(dibenzylideneacetone)dipalladium(0) (28.3 mg; 0.03 mmol). The resulting mixture was heated to 110° C. for 30 min. in a microwave. After cooling to room temperature 5% aqueous NaHCO3 was added and the mixture extracted with EtOAc. The combined organic layers were dried (Na2SO4), filtered and concentrated in vacuo. The residue was purified by column chromatography (SiO2, Et2O/hexanes 1:1) to afford 2-[4-(4-Benzyl-morpholin-2-yl)-phenyl]-1-phenyl-ethanone (110.00 mg).

Workup

  1. additionwas added
  2. extractionthe mixture extracted with EtOAc
  3. dry with materialThe combined organic layers were dried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by column chromatography (SiO2, Et2O/hexanes 1:1)

Sources & evidence

ORD record
ord-e9a9a9448ea142ed883e4d7fea92b3f8
Source dataset
uspto-grants-2015_06
Patent number
US09045441B2

Reaction notes

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