Hydrazine hydrate (1:1) → Ethyl 2-(aminomethyl)morpholine-4-carboxylate

HRID 1608214Notes

Reaction equation

HRID 1608214 reaction equation
[CH2:1]([O:3][C:4]([N:6]1[CH2:11][CH2:10][O:9][CH:8]([CH2:12][N:13]2C(=O)C3=CC=CC=C3C2=O)[CH2:7]1)=[O:5])[CH3:2].O.NN>C(O)C>[NH2:13][CH2:12][CH:8]1[O:9][CH2:10][CH2:11][N:6]([C:4]([O:3][CH2:1][CH3:2])=[O:5])[CH2:7]1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 14877394HCID 14877394, compound

Product 1

HCID 14877395Ethyl 2-(aminomethyl)morpholine-4-carboxylateYield 98.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of N-[(4-ethoxycarbonyl-2-morpholinyl)methyl]phthalimide (10.0 g), 85% hydrazine hydrate (2.9 g), and ethanol (10 ml) is refluxed with stirring for 10 minutes. The reaction mixture is filtered and the filtrate is extracted with chloroform. The organic layer is washed successively with water and saturated aqueous sodium chloride solution, and dried over magnesium sulfate. Removal of the solvent under reduced pressure gives the title compound (5.8 g) as an oil.

Workup

  1. temperatureis refluxed
  2. filtrationThe reaction mixture is filtered
  3. extractionthe filtrate is extracted with chloroform
  4. washThe organic layer is washed successively with water and saturated aqueous sodium chloride solution
  5. dry with materialdried over magnesium sulfate
  6. customRemoval of the solvent under reduced pressure

Sources & evidence

ORD record
ord-d5e7ea2101ec49bdb961c19b407af6f1
Source dataset
uspto-grants-1989_09
Patent number
US04870074

Reaction notes

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