Water → HCID 66936608, compound

HRID 1943686Notes

Reaction equation

HRID 1943686 reaction equation
[O:1]1[CH2:6][CH2:5][NH:4][C:3]2[CH:7]=[N:8][CH:9]=[CH:10][C:2]1=2.[CH3:11][O:12][C:13]1[CH:18]=[CH:17][C:16]([CH2:19][C:20](Cl)=[O:21])=[CH:15][CH:14]=1.C(N(CC)CC)C.O>ClCCl>[O:1]1[CH2:6][CH2:5][N:4]([C:20](=[O:21])[CH2:19][C:16]2[CH:17]=[CH:18][C:13]([O:12][CH3:11])=[CH:14][CH:15]=2)[C:3]2[CH:7]=[N:8][CH:9]=[CH:10][C:2]1=2

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 27346884-Methoxyphenylacetyl chlorideHCID 218859502H,3H,4H-pyrido[4,3-b][1,4]oxazine

Product 1

HCID 66936608HCID 66936608, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In a 10 ml flask, 3,4-dihydro-2H-pyrido[4,3-b][1,4]oxazine (100 mg, 0.73 mmol) and (4-methoxy-phenyl)-acetyl chloride (163 mg, 0.88 mmol) were dissolved in dichloromethane. Triethylamine (0.21 ml, 1.46 mmol) was added thereto and then stirred at room temperature for 2 hours. After completion of the reaction by adding water, the reaction mixture was extracted with dichloromethane. The combined organic layer was dried over anhydrous sodium sulfate (Na2SO4), filtered and evaporated under reduced pressure. The residue was purified by column chromatography on silica eluting with a solvent of dichloromethane:methanol=9:1. The fractions containing the product were collected and evaporated to obtain the target compound, i.e., 1-(2,3-dihydro-pyrido[4,3-b][1,4]oxazin-4-yl)-2-(4-methoxy-phenyl)-ethanone, as yellow liquid (198 mg, 95%).

Workup

  1. customAfter completion of the reaction
  2. extractionthe reaction mixture was extracted with dichloromethane
  3. dry with materialThe combined organic layer was dried over anhydrous sodium sulfate (Na2SO4)
  4. filtrationfiltered
  5. customevaporated under reduced pressure
  6. customThe residue was purified by column chromatography on silica eluting with a solvent of dichloromethane
  7. additionThe fractions containing the product
  8. customwere collected
  9. customevaporated

Sources & evidence

ORD record
ord-24092b48212848ae8ebdfca59b28beb5
Source dataset
uspto-grants-2013_03
Patent number
US08394792B2

Reaction notes

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