HCID 20097020, compound → HCID 16747054, compound

HRID 1769616Notes

Reaction equation

HRID 1769616 reaction equation
[H-].[H-].[H-].[H-].[Al+3].[Li+].[CH3:7][N:8]1[C:12]([NH:13][C:14](=O)[CH2:15][CH2:16][N:17]2[CH2:22][CH2:21][N:20]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=3[O:29][CH3:30])[CH2:19][CH2:18]2)=[CH:11][C:10]([CH3:32])=[N:9]1>O1CCCC1>[CH3:7][N:8]1[C:12]([NH:13][CH2:14][CH2:15][CH2:16][N:17]2[CH2:22][CH2:21][N:20]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=3[O:29][CH3:30])[CH2:19][CH2:18]2)=[CH:11][C:10]([CH3:32])=[N:9]1

Participants

4

Reactant 2

HCID 20097020HCID 20097020, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 16747054HCID 16747054, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

0.5 g (13 mmol) of lithium aluminum tetrahydride are suspended in 100 ml of tetrahydrofuran and a solution of 3.9 g (11 mmol) of 1,3-dimethyl-5-{3-[4-(2-methoxyphenyl)-1-piperazinyl]-propionamido}-1H-pyrazole in 50 ml of tetrahydrofuran is added dropwise in the course of 30 minutes. The mixture is kept at ambient temperature during the addition and is then refluxed for 3 hours. The excess lithium aluminum hydride is destroyed, the insoluble inorganic fraction is filtered off, the tetrahydrofuran is removed, the product is dissolved in chloroform, washed with water, dried over anhydrous sodium sulphate and evaporated to dryness and 3 g (81%) of 1,3-dimethyl-5-{3-[4-(2-methoxyphenyl)-1-piperazinyl]-propylamino}-1H-pyrazole are obtained.

Workup

  1. additionThe mixture is kept at ambient temperature during the addition
  2. temperatureis then refluxed for 3 hours
  3. customThe excess lithium aluminum hydride is destroyed
  4. filtrationthe insoluble inorganic fraction is filtered off
  5. customthe tetrahydrofuran is removed
  6. dissolutionthe product is dissolved in chloroform
  7. washwashed with water
  8. dry with materialdried over anhydrous sodium sulphate
  9. customevaporated to dryness and 3 g (81%) of 1,3-dimethyl-5-{3-[4-(2-methoxyphenyl)-1-piperazinyl]-propylamino}-1H-pyrazole
  10. customare obtained

Sources & evidence

ORD record
ord-f0924b288fcf4c919b3ad7b6cadbbf1e
Source dataset
uspto-grants-1995_01
Patent number
US05382586

Reaction notes

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