Ethyl 2-Morpholinoacetate → 4-Morpholineacetic acid

HRID 64068Notes

Reaction equation

HRID 64068 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 96.3%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

The solution of ethyl 2-morpholinoacetate (1 g, 57.8 mmol, 1.0 eq) in 8 N HCl was stirred at 95° C. for 16 h. The mixture was concentrated and quenched and extracted as in Intermediate Example 15(b). The solvent was distilled off to afford the product in 96.3% yield (0.8 g). LC-MS (ESI): Calculated mass: 145.16; Observed mass: 146.3 [M+H]+ (rt: 0.21 min).

Workup

  1. concentrationThe mixture was concentrated
  2. customquenched
  3. extractionextracted as in Intermediate Example 15(b)
  4. distillationThe solvent was distilled off
  5. customto afford the product in 96.3% yield (0.8 g)
  6. custom146.3 [M+H]+ (rt: 0.21 min)

Sources & evidence

ORD record
ord-38f6cf73f2144ea18b2ff573ed1a9291
Source dataset
uspto-grants-2016_09
Patent number
US09447091B2

Reaction notes

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