Ethyl bromoacetate → Ethyl 2-Morpholinoacetate

HRID 64067Notes

Reaction equation

HRID 64067 reaction equation
[NH:1]1[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.C([O-])([O-])=O.[K+].[K+].Br[CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16]>CN(C=O)C>[O:4]1[CH2:5][CH2:6][N:1]([CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16])[CH2:2][CH2:3]1

Participants

5

Reactant 3

HCID 7748Ethyl bromoacetateHCID 8083MorpholineHCID 11430Potassium Carbonate

Product 1

HCID 2734105Ethyl 2-MorpholinoacetateYield 71.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of morpholine (1.4 g, 16.3 mmol, 1.0 eq) in DMF were added K2CO3 (5.63 g, 40.7 mmol, 2.5 eq.) and ethyl 2-bromoacetate (4.07 g, 24.4 mmol, 1.5 eq.). The mixture was stirred at RT for 16 h and quenched and extracted as in Intermediate Example 5(a). The solvent was distilled off to afford the product in 71.4% yield (2 g). LC-MS (ESI): Calculated mass: 173.2; Observed mass: 174.0 [M+H]+ (rt: 0.20 min).

Workup

  1. customquenched
  2. extractionextracted as in Intermediate Example 5(a)
  3. distillationThe solvent was distilled off
  4. customto afford the product in 71.4% yield (2 g)
  5. custom174.0 [M+H]+ (rt: 0.20 min)

Sources & evidence

ORD record
ord-b079e3a10b2146dda0a2176581a0f1fd
Source dataset
uspto-grants-2016_09
Patent number
US09447091B2

Reaction notes

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