Hydrazine hydrate (1:1) → 4-[[5-Methyl-2-(1-methylethyl)phenoxy]methyl]piperidine-1-propylamine

HRID 37190Notes

Reaction equation

HRID 37190 reaction equation
[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([CH:30]([CH3:32])[CH3:31])=[C:6]([CH:29]=1)[O:7][CH2:8][CH:9]1[CH2:14][CH2:13][N:12]([CH2:15][CH2:16][CH2:17][N:18]2C(=O)C3C(=CC=CC=3)C2=O)[CH2:11][CH2:10]1.O.NN>C(O)C>[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([CH:30]([CH3:32])[CH3:31])=[C:6]([CH:29]=1)[O:7][CH2:8][CH:9]1[CH2:14][CH2:13][N:12]([CH2:15][CH2:16][CH2:17][NH2:18])[CH2:11][CH2:10]1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 199348062-[3-[4-[[5-Methyl-2-(1-methylethyl)phenoxy]methyl]piperid-1-yl]propyl]-1H-isoindole-1,3(2H)-dione

Product 1

HCID 156701034-[[5-Methyl-2-(1-methylethyl)phenoxy]methyl]piperidine-1-propylamine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

17.35 g (0.04 mol) of 2-[3-[4-[[5-methyl-2-(1-methylethyl)phenoxy]methyl]piperid-1-yl]propyl]-1H-isoindole-1,3 (2H)-dione are reacted in 340 ml of ethanol with 3.9 ml (0.08 mol) of hydrazine hydrate. The mixture is heated at the reflux temperature for 3 h. The mixture is filtered, the solid being rinsed with a small amount of ethanol, the filtrate is concentrated and taken up in diethyl ether. An insoluble material is again removed by filtration and the filtrate is again concentrated. The insoluble materials are combined in a round-bottomed flask and 25 ml of concentrated hydrochloric acid and 75 ml of water are added. The mixture is brought to reflux for 2 h while stirring. It is allowed to cool, the insoluble material is removed by filtration, rinsing is carried out with water, basification is carried out with concentrated aqueous ammonia and extraction is carried out three times with diethyl ether. The organic phase is dried over sodium sulphate, filtered and concentrated under reduced pressure. A compound is obtained which is used as is in the following stage.

Workup

  1. temperatureThe mixture is heated at the reflux temperature for 3 h
  2. filtrationThe mixture is filtered
  3. washthe solid being rinsed with a small amount of ethanol
  4. concentrationthe filtrate is concentrated
  5. customAn insoluble material is again removed by filtration
  6. concentrationthe filtrate is again concentrated
  7. customThe insoluble materials are combined in a round-bottomed flask
  8. addition25 ml of concentrated hydrochloric acid and 75 ml of water are added
  9. temperatureto reflux for 2 h
  10. temperatureto cool
  11. customthe insoluble material is removed by filtration
  12. washrinsing
  13. extractionis carried out with concentrated aqueous ammonia and extraction
  14. dry with materialThe organic phase is dried over sodium sulphate
  15. filtrationfiltered
  16. concentrationconcentrated under reduced pressure
  17. customA compound is obtained which

Sources & evidence

ORD record
ord-5487c7b733cf4a14a8837a955069a46d
Source dataset
uspto-grants-1995_05
Patent number
US05420130

Reaction notes

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