Water → HCID 54146624, compound

HRID 850518Notes

Reaction equation

HRID 850518 reaction equation
[CH3:1][O:2][C:3]1[CH:11]=[CH:10][C:6]([C:7]([OH:9])=O)=[CH:5][C:4]=1[O:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17].[NH:18]1[CH2:23][CH2:22][O:21][CH2:20][CH2:19]1.O>S(Cl)(Cl)=O.CN(C=O)C>[CH3:1][O:2][C:3]1[CH:11]=[CH:10][C:6]([C:7]([N:18]2[CH2:23][CH2:22][O:21][CH2:20][CH2:19]2)=[O:9])=[CH:5][C:4]=1[O:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17]

Participants

6

Reactant 3

HCID 962WaterHCID 8083MorpholineHCID 19363244HCID 19363244, compound

Product 1

HCID 54146624HCID 54146624, compoundYield 67.9%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 24386Thionyl ChlorideSolvent

Conditions

Temperature
70 °C

Procedure

4-Methoxy-3-pentyloxybenzoic acid (250 mg, 1.05 mmol, 1 eq) was dissolved in thionyl chloride (1.05 ml) in a stream of nitrogen, and the solution was stirred at 70° C. for 5 hours. The mixture was cooled to room temperature, and excess thionyl chloride was evaporated under reduced pressure. The residue was added to a solution of morpholine (274 mg, 3.15 mol, 3.0 eq) in DMF (3 ml) under ice-cooling. The mixture was stirred under ice-cooling for 30 minutes, and then further at room temperature for 1.5 hours. Water (30 ml) was added to this reaction mixture and the mixture was extracted twice with ethyl acetate (50 ml). The organic layers were combined, washed with saturated brine (50 ml) and dried over anhydrous sodium sulfate. The drying agent was fltered off, and the filtrate was concentrated under reduced pressure. The obtained residue was purified by column chromatography on silica gel (n-hexane/ethyl acetate=2/1) to give (4-methoxy-3-pentyloxyphenyl)morpholin-4-yl-methanone (219 mg, 67.9%) as an oil

Workup

  1. temperatureThe mixture was cooled to room temperature
  2. customexcess thionyl chloride was evaporated under reduced pressure
  3. temperaturecooling
  4. stirringThe mixture was stirred under ice-
  5. temperaturecooling for 30 minutes
  6. waitfurther at room temperature for 1.5 hours
  7. extractionthe mixture was extracted twice with ethyl acetate (50 ml)
  8. washwashed with saturated brine (50 ml)
  9. dry with materialdried over anhydrous sodium sulfate
  10. concentrationthe filtrate was concentrated under reduced pressure
  11. customThe obtained residue was purified by column chromatography on silica gel (n-hexane/ethyl acetate=2/1)

Sources & evidence

ORD record
ord-61222208263341158dc3b777c90de0ad
Source dataset
uspto-grants-2000_01
Patent number
US06017919

Reaction notes

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