Morpholine → 5-(Methanesulfonyl)-2-(morpholin-4-yl)benzoic acid

HRID 1723644Notes

Reaction equation

HRID 1723644 reaction equation
Cl[C:2]1[CH:10]=[CH:9][C:8]([S:11]([CH3:14])(=[O:13])=[O:12])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[NH:15]1[CH2:20][CH2:19][O:18][CH2:17][CH2:16]1>>[CH3:14][S:11]([C:8]1[CH:9]=[CH:10][C:2]([N:15]2[CH2:20][CH2:19][O:18][CH2:17][CH2:16]2)=[C:3]([CH:7]=1)[C:4]([OH:6])=[O:5])(=[O:13])=[O:12]

Participants

3

Reactant 2

HCID 8083MorpholineHCID 23291322-Chloro-5-(methylsulphonyl)benzoic acid

Product 1

HCID 211003195-(Methanesulfonyl)-2-(morpholin-4-yl)benzoic acid

Procedure

A mixture of 163.8 mg (0.7 mmol) 2-chloro-5-methanesulfonyl-benzoic acid (example 4 step b) in 2 ml morpholine was heated for 16 h to 100° C. After evaporation of all volatiles the residue was taken up in 2 ml methanol/formic acid 3/1 and subjected to reversed phase HPLC purification eluting with an acetonitrile/water gradient to yield after evaporation of the product fractions the title compound. MS (m/e): 284.1 (M−H, 100%)

Workup

  1. temperaturewas heated for 16 h to 100° C
  2. customAfter evaporation of all volatiles the residue
  3. customsubjected to reversed phase HPLC purification
  4. washeluting with an acetonitrile/water gradient
  5. customto yield
  6. customafter evaporation of the product fractions the title compound

Sources & evidence

ORD record
ord-a3604cbf8d3f4f38aca16fb7d4486071
Source dataset
uspto-grants-2009_02
Patent number
US07485637B2

Reaction notes

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