Ethyl chloroacetate → Ethyl 2-Morpholinoacetate

HRID 64054Notes

Reaction equation

HRID 64054 reaction equation
Cl[CH2:2][C:3]([O:5][CH2:6][CH3:7])=[O:4].[C:8]([O-:11])([O-])=O.[K+].[K+].[CH3:14][N:15]1CCN[CH2:17][CH2:16]1>CN(C=O)C>[O:11]1[CH2:8][CH2:14][N:15]([CH2:2][C:3]([O:5][CH2:6][CH3:7])=[O:4])[CH2:16][CH2:17]1

Participants

5

Reactant 3

HCID 7751Ethyl chloroacetateHCID 11430Potassium CarbonateHCID 531671-Methylpiperazine

Product 1

HCID 2734105Ethyl 2-MorpholinoacetateYield 74%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of ethyl 2-chloroacetate (0.5 g, 5.74 mmol) in DMF (70 ml) at 10° C. were added K2CO3 (1.98 g, 14.34 mmol, 2.5 eq.) and 1-methylpiperazine (1.05 g, 8.6 mmol, 1.5 eq.) and the mixture was stirred at RT for 2 h. The mixture was quenched and extracted as in Intermediate Example 5(c). The solvent was distilled off and the crude residue was purified by column chromatography (60-120 silica gel, 40% ethyl acetate in hexane) to afford the product in 74% yield (0.74 g). LC-MS (ESI): Calculated mass: 173.2, Observed mass: 174.0 [M+H]+ (rt: 0.20 min).

Workup

  1. customThe mixture was quenched
  2. extractionextracted as in Intermediate Example 5(c)
  3. distillationThe solvent was distilled off
  4. customthe crude residue was purified by column chromatography (60-120 silica gel, 40% ethyl acetate in hexane)
  5. customto afford the product in 74% yield (0.74 g)
  6. custom174.0 [M+H]+ (rt: 0.20 min)

Sources & evidence

ORD record
ord-84ae1cb296dd4b1789b771fc872172c6
Source dataset
uspto-grants-2016_09
Patent number
US09447091B2

Reaction notes

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