Morpholine → 2-Morpholin-4-ylmethyl-acrylic acid methyl ester

HRID 1038069Notes

Reaction equation

HRID 1038069 reaction equation
Br[CH2:2][C:3](=[CH2:8])[C:4]([O:6][CH3:7])=[O:5].C([O-])([O-])=O.[K+].[K+].[NH:15]1[CH2:20][CH2:19][O:18][CH2:17][CH2:16]1>C(#N)C>[CH3:7][O:6][C:4](=[O:5])[C:3]([CH2:2][N:15]1[CH2:20][CH2:19][O:18][CH2:17][CH2:16]1)=[CH2:8]

Participants

5

Reactant 3

HCID 8083MorpholineHCID 11430Potassium CarbonateHCID 5210932-Propenoic acid, 2-(bromomethyl)-, methyl ester

Product 1

HCID 589464832-Morpholin-4-ylmethyl-acrylic acid methyl ester

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a mixture of methyl 2-(bromomethyl)acrylate (119 μl, 1 mmol) and K2CO3 (138 mg, 1 eq) in acetonitrile (2 ml) was added morpholine (96 μl, 1.1 mmols). The mixture was stirred overnight, filtered and concentrated. The residue was partitioned between ether and water, and organic layer was isolated, washed with brine and dried (MgSO4). Solvent was removed and residue was purified by column chromatography. Ethyl acetate eluted out the title compound as clear oil (110 mg, 59%).

Workup

  1. filtrationfiltered
  2. concentrationconcentrated
  3. customThe residue was partitioned between ether and water
  4. customorganic layer was isolated
  5. washwashed with brine
  6. dry with materialdried (MgSO4)
  7. customSolvent was removed
  8. customresidue was purified by column chromatography
  9. washEthyl acetate eluted out the title compound as clear oil (110 mg, 59%)

Sources & evidence

ORD record
ord-f010b168305549fcbce523d6ba509550
Source dataset
uspto-grants-2013_10
Patent number
US08546404B2

Reaction notes

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