Morpholine → HCID 559409, compound

HRID 524391Notes

Reaction equation

HRID 524391 reaction equation
Cl[S:2]([C:5]1[CH:10]=[CH:9][C:8]([CH2:11][C:12]([O:14][CH3:15])=[O:13])=[CH:7][CH:6]=1)(=[O:4])=[O:3].[NH:16]1[CH2:21][CH2:20][O:19][CH2:18][CH2:17]1.C(N(CC)CC)C>C(Cl)Cl>[O:19]1[CH2:20][CH2:21][N:16]([S:2]([C:5]2[CH:10]=[CH:9][C:8]([CH2:11][C:12]([O:14][CH3:15])=[O:13])=[CH:7][CH:6]=2)(=[O:4])=[O:3])[CH2:17][CH2:18]1

Participants

5

Reactant 3

HCID 8083MorpholineHCID 8471TriethylamineHCID 23388822methyl 2-(4-(chlorosulfonyl)phenyl)acetate

Product 1

HCID 559409HCID 559409, compoundYield 62.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
2.5 °C

Procedure

Methyl 2-(4-chlorosulfonylphenyl)acetate (2.0 g, 8.04 mmol) was taken in dry DCM (50 mL) under argon atmosphere and cooled to 0-5° C., morpholine (0.77 mL, 8.84 mmol) followed by triethylamine (1.16 mL, 8.84 mmol) was added dropwise to the mixture at 0-5° C. Reaction mixture was then brought to room temperature and stirred for additional 2 hours. Reaction mixture was washed with water followed by brine solution, dried over anhydrous sodium sulfate and concentrated under reduced pressure to give the crude product, which was purified by column chromatography using 14-20% ethyl acetate in hexane as eluent to give Methyl 2-(4-morpholinosulfonylphenyl)acetate (1.5 g).

Workup

  1. additionwas added dropwise to the mixture at 0-5° C
  2. customReaction mixture
  3. customwas then brought to room temperature
  4. customReaction mixture
  5. washwas washed with water
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customto give the crude product, which
  9. customwas purified by column chromatography

Sources & evidence

ORD record
ord-70ee2080e4ea40f0aace94ebd97e195a
Source dataset
uspto-grants-2016_05
Patent number
US09340506B2

Reaction notes

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