Ethyl 2-Morpholinoacetate → 4-Morpholineacetic acid

HRID 64077Notes

Reaction equation

HRID 64077 reaction equation
[O:1]1[CH2:6][CH2:5][N:4]([CH2:7][C:8]([O:10]CC)=[O:9])[CH2:3][CH2:2]1>Cl>[O:1]1[CH2:6][CH2:5][N:4]([CH2:7][C:8]([OH:10])=[O:9])[CH2:3][CH2:2]1

Participants

3

Reactant 1

HCID 2734105Ethyl 2-Morpholinoacetate

Product 1

HCID 4389684-Morpholineacetic acidYield 60%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

The solution of ethyl 2-morpholinoacetate (0.73 g, 4.24 mmol, 1.0 eq) in 8 N HCl was stirred at 95° C. for 16 h. The mixture was concentrated on vacuum pump and quenched and extracted as in Intermediate Example 15(b). The solvent was distilled off to afford the product in 60% yield (0.37 g). LC-MS (ESI): Calculated mass: 145.1; Observed mass 146.3 [M+H]+ (rt: 0.28 min).

Workup

  1. concentrationThe mixture was concentrated on vacuum pump
  2. customquenched
  3. extractionextracted as in Intermediate Example 15(b)
  4. distillationThe solvent was distilled off
  5. customto afford the product in 60% yield (0.37 g)
  6. customObserved mass 146.3 [M+H]+ (rt: 0.28 min)

Sources & evidence

ORD record
ord-1a70147cae1944d58500d429263efef5
Source dataset
uspto-grants-2016_09
Patent number
US09447091B2

Reaction notes

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