Hydrazine hydrate (1:1) → 2-Acetylaminomethyl-4-(2-chlorobenzyl)-6-methylmorpholine

HRID 1608227Notes

Reaction equation

HRID 1608227 reaction equation
[Cl:1][C:2]1[CH:27]=[CH:26][CH:25]=[CH:24][C:3]=1[CH2:4][N:5]1[CH2:10][CH:9]([CH3:11])[O:8][CH:7]([CH2:12][N:13]2C(=O)C3=CC=CC=[C:15]3[C:14]2=[O:23])[CH2:6]1.O.NN>C(O)C>[C:14]([NH:13][CH2:12][CH:7]1[O:8][CH:9]([CH3:11])[CH2:10][N:5]([CH2:4][C:3]2[CH:24]=[CH:25][CH:26]=[CH:27][C:2]=2[Cl:1])[CH2:6]1)(=[O:23])[CH3:15]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 19848602N-[[4-(2-chlorobenzyl)-6-methyl-2-morpholinyl]methyl]phthalimide

Product 1

HCID 198486042-Acetylaminomethyl-4-(2-chlorobenzyl)-6-methylmorpholineYield 74.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of N-[[4-(2-chlorobenzyl)-6-methyl-2-morpholinyl]methyl]phthalimide (26 g), 100% hydrazine hydrate (4.2 g), and ethanol (20 ml) is refluxed with stirring for 15 minutes. After the insoluble materials are filtered off, the filtrate is diluted with water and extracted with chloroform. The organic layer is washed successively with water and saturated aqueous sodium chloride solution, dried over magnesium sulfate, and filtered. Acetic anhydride (14.7 g) is added to the filtrate, and the 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. After removal of the solvent under reduced pressure, the residue is chromatographed on silica gel with ethyl acetate to give the title compound (15 g) as an oil.

Workup

  1. temperatureis refluxed
  2. filtrationAfter the insoluble materials are filtered off
  3. additionthe filtrate is diluted with water
  4. extractionextracted with chloroform
  5. washThe organic layer is washed successively with water and saturated aqueous sodium chloride solution
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. additionAcetic anhydride (14.7 g) is added to the filtrate
  9. stirringthe mixture is stirred at 25° C. for 2 hours
  10. washThe reaction mixture is washed successively with aqueous sodium hydroxide solution, water and saturated aqueous sodium chloride solution
  11. dry with materialdried over magnesium sulfate
  12. customAfter removal of the solvent under reduced pressure
  13. customthe residue is chromatographed on silica gel with ethyl acetate

Sources & evidence

ORD record
ord-cb198b78b670468b8f21b25adda362c3
Source dataset
uspto-grants-1989_09
Patent number
US04870074

Reaction notes

Loading…