Hydrazine hydrate (1:1) → n-((4-Benzylmorpholin-2-yl)methyl)acetamide

HRID 1608208Notes

Reaction equation

HRID 1608208 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][O:11][CH:10]([CH2:14][N:15]2C(=O)C3=CC=CC=[C:17]3[C:16]2=[O:25])[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O.NN>C(O)C>[C:16]([NH:15][CH2:14][CH:10]1[O:11][CH2:12][CH2:13][N:8]([CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[CH2:9]1)(=[O:25])[CH3:17]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 117245602-((4-benzylmorpholin-2-yl)methyl)-2,3-dihydro-1H-isoindole-1,3-dione

Product 1

HCID 14877386n-((4-Benzylmorpholin-2-yl)methyl)acetamideYield 84.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of N-[(4-benzyl-2-morpholinyl)methyl]phthalimide (162 g), 85% hydrazine hydrate (43.3 g), and ethanol (100 ml) is refluxed with stirring for 20 minutes. The reaction mixture is filtered, and the filtrate is diluted with water and extracted with chloroform. The organic layer is separated, washed with a small amount of water and then with saturated aqueous sodium chloride solution, dried over magnesium sulfate, and filtered. To the filtrate is added slowly acetic anhydride (98.3 g), and the resulting mixture is stirred at 25° C. for 2 hours. The reaction mixture is washed successively with aqueous sodium hydroxide solution, water and saturated aqueous sodium chloride solution, and dried over magnesium sulfate. The solvent is distilled off under reduced pressure, and the residue is recrystallized from toluene to give the title compound (101 g), mp 110°-111° C.

Workup

  1. temperatureis refluxed
  2. filtrationThe reaction mixture is filtered
  3. additionthe filtrate is diluted with water
  4. extractionextracted with chloroform
  5. customThe organic layer is separated
  6. washwashed with a small amount of water
  7. dry with materialwith saturated aqueous sodium chloride solution, dried over magnesium sulfate
  8. filtrationfiltered
  9. additionTo the filtrate is added slowly acetic anhydride (98.3 g)
  10. stirringthe resulting mixture is stirred at 25° C. for 2 hours
  11. washThe reaction mixture is washed successively with aqueous sodium hydroxide solution, water and saturated aqueous sodium chloride solution
  12. dry with materialdried over magnesium sulfate
  13. distillationThe solvent is distilled off under reduced pressure
  14. customthe residue is recrystallized from toluene

Sources & evidence

ORD record
ord-b16882bcc51f49b8b63b80abe3db2f2a
Source dataset
uspto-grants-1989_09
Patent number
US04870074

Reaction notes

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