Morpholine → Ethyl 2-Morpholinoacetate

HRID 352202Notes

Reaction equation

HRID 352202 reaction equation
Br[CH2:2][CH2:3][O:4][C:5](=[O:7])[CH3:6].C(=O)([O-])[O-].[K+].[K+].[NH:14]1[CH2:19][CH2:18][O:17][CH2:16][CH2:15]1>O1CCCC1>[CH2:3]([O:4][C:5](=[O:7])[CH2:6][N:14]1[CH2:19][CH2:18][O:17][CH2:16][CH2:15]1)[CH3:2]

Participants

5

Reactant 3

HCID 8083MorpholineHCID 11430Potassium CarbonateHCID 135641-Acetoxy-2-bromoethane

Product 1

HCID 2734105Ethyl 2-MorpholinoacetateYield 53%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of bromoethylacetate, 3.3 mL (30.0 mmol) in 100 mL of tetrahydrofuran was added 4.14 g (30.0 mmol) of potassium carbonate and 2.6 mL (30.0 mmol) of morpholine. The reaction mixture stirred overnight at rt. and was concentrated to dryness. The residue was partitioned between 20% isopropanol/chloroformn and saturated aqueous NaHCO3. The mixture was washed with saturated NaHCO3, washed with brine, dried over Na2SO4, filtered and concentrated to dryness to give 2.75 g (53%) of the desired product as a tan oil. MS (ion spray) 174.2 (M+).

Workup

  1. concentrationand was concentrated to dryness
  2. customThe residue was partitioned between 20% isopropanol/chloroformn and saturated aqueous NaHCO3
  3. washThe mixture was washed with saturated NaHCO3
  4. washwashed with brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-3b6c946d75ea477b9e3ec6c83871455c
Source dataset
uspto-grants-2004_06
Patent number
US06743794B2

Reaction notes

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