Diethyl Ether → HCID 10221341, compound

HRID 2396449Notes

Reaction equation

HRID 2396449 reaction equation
[CH3:1][C:2]([N:4]1[CH2:9][CH2:8][N:7]([CH2:10][C:11]2[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[C:13]([O:19][CH3:20])[C:12]=2[O:21]C)[CH2:6][CH2:5]1)=O.C(OCC)C.[H-].[H-].[H-].[H-].[Li+].[Al+3].[OH-].[Na+]>O>[CH2:2]([N:4]1[CH2:9][CH2:8][N:7]([CH2:10][C:11]2[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[C:13]([O:19][CH3:20])[C:12]=2[OH:21])[CH2:6][CH2:5]1)[CH3:1]

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 37642979HCID 37642979, compound

Product 1

HCID 10221341HCID 10221341, compoundYield 64.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

##STR6## 30.8 g (0.1 mol) of N-acetyltrimetazidine, 600 ml of diethyl ether and 11.1 g (0.3 mol) of LiAlH4 are heated to and then maintained at reflux for 24 hours with vigorous stirring, the mixture is subsequently allowed to return to room temperature, and stirring is continued for a further 12 hours, after which the mixture is hydrolysed in succession with 10 ml of water, 10 ml of 4N sodium hydroxide solution and finally 30 ml of water. The mixture is filtered and the residue is washed three times with 200 ml of diethyl ether each time. The ethereal phases are removed and the residue is then taken up three times with 300 ml of CH2C2 each time. The organic phase obtained after filtration is dried over magnesium sulphate, and the solvent is then removed by evaporation in vacuo. The residue (approximately 20 g) is filtered over 150 g of silica using a mixture of chloroform and ethanol (97.5% -2.5%) as eluants. 18 g of N-ethyl-N'-(2-hydroxy-3,4-dimethoxybenzyl)-piperazine are obtained directly (yield: 64%).

Workup

  1. temperaturethen maintained
  2. temperatureat reflux for 24 hours with vigorous stirring
  3. customto return to room temperature
  4. filtrationThe mixture is filtered
  5. washthe residue is washed three times with 200 ml of diethyl ether each time
  6. customThe ethereal phases are removed
  7. customThe organic phase obtained
  8. filtrationafter filtration
  9. dry with materialis dried over magnesium sulphate
  10. customthe solvent is then removed by evaporation in vacuo
  11. filtrationThe residue (approximately 20 g) is filtered over 150 g of silica using
  12. additiona mixture of chloroform and ethanol (97.5% -2.5%) as eluants

Sources & evidence

ORD record
ord-17773f256c8d4220be53981ed9acaf94
Source dataset
uspto-grants-1996_02
Patent number
US05492913

Reaction notes

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