Morpholine → 2-[(4-Tolylsulfonyl)oxy]propionic acid morpholide

HRID 255946Notes

Reaction equation

HRID 255946 reaction equation
[C:1]1([CH3:16])[CH:6]=[CH:5][C:4]([S:7]([O:10][CH:11]([CH3:15])[C:12](Cl)=[O:13])(=[O:9])=[O:8])=[CH:3][CH:2]=1.[NH:17]1[CH2:22][CH2:21][O:20][CH2:19][CH2:18]1>O1CCCC1>[C:1]1([CH3:16])[CH:6]=[CH:5][C:4]([S:7]([O:10][CH:11]([CH3:15])[C:12]([N:17]2[CH2:22][CH2:21][O:20][CH2:19][CH2:18]2)=[O:13])(=[O:9])=[O:8])=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 8083MorpholineHCID 12761564HCID 12761564, compound

Product 1

HCID 229287122-[(4-Tolylsulfonyl)oxy]propionic acid morpholide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

7.5 g (30 mmol) of 2-[(4-tolylsulfonyl)oxy]-propionyl chloride are dissolved in 15 ml of tetrahydrofuran in a flask. 6.5 g (80 mmol) of morpholine are then slowly added dropwise at 0°-5° C., with stirring and simultaneous cooling. The mixture is then subsequently stirred at 0° C., poured onto ice and extracted with diethyl ether. The organic phase is separated off, dried with Na2SO4 and concentrated in a rotary vacuum evaporator. The light yellow residue is separated on a silica gel column (eluting agent: hexane/ethyl acetate 1:1). White crystals of melting point 75°-77° C. then result.

Workup

  1. stirringThe mixture is then subsequently stirred at 0° C.
  2. additionpoured onto ice
  3. extractionextracted with diethyl ether
  4. customThe organic phase is separated off
  5. dry with materialdried with Na2SO4
  6. concentrationconcentrated in a rotary vacuum evaporator
  7. customThe light yellow residue is separated on a silica gel column (eluting agent: hexane/ethyl acetate 1:1)
  8. customWhite crystals of melting point 75°-77° C. then result

Sources & evidence

ORD record
ord-fb3b7aaaf9e14a7e9f92d86615a614fb
Source dataset
uspto-grants-1987_10
Patent number
US04699949

Reaction notes

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