Morpholine → HCID 730215, compound

HRID 912169Notes

Reaction equation

HRID 912169 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[CH3:11])[C:5]([OH:7])=O.[NH:12]1[CH2:17][CH2:16][O:15][CH2:14][CH2:13]1.[Cl-].[NH4+]>ClCCl>[Br:1][C:2]1[CH:3]=[C:4]([C:5]([N:12]2[CH2:17][CH2:16][O:15][CH2:14][CH2:13]2)=[O:7])[CH:8]=[CH:9][C:10]=1[CH3:11]

Participants

5

Reactant 3

HCID 8083MorpholineHCID 25517Ammonium ChlorideHCID 821303-Bromo-4-methylbenzoic acid

Product 1

HCID 730215HCID 730215, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To dichloromethane solution (2 ml) of 3-bromo-4-methylbenzoic acid (50 mg, 0.23 mmol), WSCI (67 mg, 0.348 mmol), morpholine (24 μl, 0.278 mmol) and N,N-dimethylaminopyridine (28 mg, 0.232 mmol) were added, followed by stirring at room temperature for 16 hours. To the reaction mixture, saturated aqueous ammonium chloride solution was added, followed by extraction twice with ethyl acetate (10 ml). The organic layer was washed with brine (10 ml), and dried over sodium sulfate, followed by distilling off under reduced pressure, and the resulting residue was purified by silica gel column chromatography (dichloromethane/methanol=50/1), whereby (3-bromo-4-methyl-phenyl)-morpholin-4-yl-methanone was obtained as a yellow brown solid (68 mg, 100%).

Workup

  1. extractionfollowed by extraction twice with ethyl acetate (10 ml)
  2. washThe organic layer was washed with brine (10 ml)
  3. dry with materialdried over sodium sulfate
  4. distillationby distilling off under reduced pressure
  5. customthe resulting residue was purified by silica gel column chromatography (dichloromethane/methanol=50/1)

Sources & evidence

ORD record
ord-11726721e42d43b3a65a76c328a2f651
Source dataset
uspto-grants-2011_09
Patent number
US08022205B2

Reaction notes

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