Ethyl chloroacetate → Ethyl 2-Morpholinoacetate

HRID 64076Notes

Reaction equation

HRID 64076 reaction equation
[NH:1]1[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.C([O-])([O-])=O.[K+].[K+].Cl[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 7751Ethyl chloroacetateHCID 8083MorpholineHCID 11430Potassium Carbonate

Product 1

HCID 2734105Ethyl 2-MorpholinoacetateYield 73.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of morpholine (0.5 g, 5.739 mmol, 1.0 eq) in DMF were added K2CO3 (1.98 g, 14.34 mmol, 2.5 eq.) and ethyl 2-chloroacetate (1.05 g, 8.60 mmol, 1.5 eq.). The mixture was stirred at RT for 12 h. The mixture was quenched and extracted as in Intermediate Example 5(a). The solvent was distilled off to afford the product in 73.9% yield (0.735 g). LC-MS (ESI): Calculated mass: 173.21; Observed mass 174.0 [M+H]+ (rt: 0.1-0.4 min).

Workup

  1. customThe mixture was quenched
  2. extractionextracted as in Intermediate Example 5(a)
  3. distillationThe solvent was distilled off
  4. customto afford the product in 73.9% yield (0.735 g)
  5. customObserved mass 174.0 [M+H]+ (rt: 0.1-0.4 min)

Sources & evidence

ORD record
ord-bfdce75122a84f659de3c1baab96175c
Source dataset
uspto-grants-2016_09
Patent number
US09447091B2

Reaction notes

Loading…