Morpholine → Methyl 4-(morpholin-4-ylmethyl)benzoate

HRID 2421353Notes

Reaction equation

HRID 2421353 reaction equation
Br[CH2:2][C:3]1[CH:12]=[CH:11][C:6]([C:7]([O:9][CH3:10])=[O:8])=[CH:5][CH:4]=1.[NH:13]1[CH2:18][CH2:17][O:16][CH2:15][CH2:14]1>CN(C)C=O>[N:13]1([CH2:2][C:3]2[CH:12]=[CH:11][C:6]([C:7]([O:9][CH3:10])=[O:8])=[CH:5][CH:4]=2)[CH2:18][CH2:17][O:16][CH2:15][CH2:14]1

Participants

4

Reactant 2

HCID 8083MorpholineHCID 256687Methyl 4-(bromomethyl)benzoate

Product 1

HCID 10466592Methyl 4-(morpholin-4-ylmethyl)benzoate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of methyl 4-bromomethylbenzoate (14.75 g) in dimethylformamide (50 ml), cooled to 5° C., was added rapidly morpholine (13.8 ml). The mixture was stirred at room temperature for 2 h. The mixture was partitioned between diethyl ether and water. The organic layer was washed with water, dried (MgSO4), evaporated and purified by column chromatography eluting with ethyl acetate/iso-hexane (20:80) to give methyl 4-(morpholin-4-ylmethyl)benzoate (14.13 g) as an oil.

Workup

  1. customThe mixture was partitioned between diethyl ether and water
  2. washThe organic layer was washed with water
  3. dry with materialdried (MgSO4)
  4. customevaporated
  5. custompurified by column chromatography
  6. washeluting with ethyl acetate/iso-hexane (20:80)

Sources & evidence

ORD record
ord-4274850a1934431aabae478d225da322
Source dataset
uspto-grants-2011_06
Patent number
US07956084B2

Reaction notes

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