Water → C-(1-Benzyl-4-phenyl-piperazin-2-yl)-methylamine

HRID 728910Notes

Reaction equation

HRID 728910 reaction equation
[C:1]1([N:7]2[CH2:12][CH2:11][N:10]([CH2:13][C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[CH:9]([C:20]([NH2:22])=O)[CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[OH-].[Na+]>O1CCCC1.C(Cl)Cl.CO>[C:1]1([N:7]2[CH2:12][CH2:11][N:10]([CH2:13][C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[CH:9]([CH2:20][NH2:22])[CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

7

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 109900971-Benzyl-4-phenyl-piperazine-2-carboxamideHCID 21226445Aluminium lithium hydride

Product 1

HCID 11044210C-(1-Benzyl-4-phenyl-piperazin-2-yl)-methylamine

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 21226129Dichloromethane methanolSolvent

Procedure

To 4-phenyl-1-(phenylmethyl)-2-piperazinecarboxamide (28.5 g, 96 mmol) dissolved in tetrahydrofuran (220 mL) add lithium aluminum hydride (9.0 g,0.24 mol) portionwise. Stir and heat the reaction to reflux. Monitor the progress of the reaction by thin-layer chromatography. Upon completion, slowly add water (9 mL), 2N NaOH (9 ml), and H2O (27 mL). Suction filter the slurry through celite and wash the pad with ethyl acetate (500 mL). Remove the solvent in vacuo to give a brown oil. Flash chromatograph the oil on silica (400 g) with 19/1 CH2Cl2 /MeOH to give the title compound.

Workup

  1. temperatureheat
  2. customthe reaction
  3. temperatureto reflux
  4. customMonitor the progress of the reaction by thin-layer chromatography
  5. filtrationSuction filter the slurry through celite
  6. washwash the pad with ethyl acetate (500 mL)
  7. customRemove the solvent in vacuo
  8. customto give a brown oil

Sources & evidence

ORD record
ord-bbc730e13d2b45689e2655626dd1ad14
Source dataset
uspto-grants-1991_09
Patent number
US05051422

Reaction notes

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