Sodium Hydroxide → 4-((4-(Aminomethyl)phenyl)methyl)-1-phenylpiperazine

HRID 1282051Notes

Reaction equation

HRID 1282051 reaction equation
[C:1]1([N:7]2[CH2:12][CH2:11][N:10]([CH2:13][C:14]3[CH:19]=[CH:18][C:17]([CH2:20][NH:21]C(=O)C)=[CH:16][CH:15]=3)[CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH-].[Na+]>Cl>[NH2:21][CH2:20][C:17]1[CH:16]=[CH:15][C:14]([CH2:13][N:10]2[CH2:9][CH2:8][N:7]([C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)[CH2:12][CH2:11]2)=[CH:19][CH:18]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 11652722N-(4-((4-Phenylpiperazin-1-yl)methyl)phenylmethyl)acetamide

Product 1

HCID 184230964-((4-(Aminomethyl)phenyl)methyl)-1-phenylpiperazineYield 59.2%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

N-(4-((4-Phenylpiperazin-1-yl)methyl)phenylmethyl)acetamide (2.6 g) was dissolved in 10% hydrochloric acid (50 ml) and the mixture was refluxed under heating for 6 hr. To the mixture was added 10% aqueous sodium hydroxide solution to make it alkaline and the mixture was extracted with ethyl acetate (100 ml×3). The extract was washed with saturated brine and dried over anhydrous sodium sulfate. The solvent was evaporated and the obtained residue was crystallized from water-ethanol to give the title compound (1.34 g) as white crystals, m.p.=68-70° C.

Workup

  1. temperaturethe mixture was refluxed
  2. temperatureunder heating for 6 hr
  3. extractionthe mixture was extracted with ethyl acetate (100 ml×3)
  4. washThe extract was washed with saturated brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. customThe solvent was evaporated
  7. customthe obtained residue was crystallized from water-ethanol

Sources & evidence

ORD record
ord-ace00c96500b4eb095c768561816041d
Source dataset
uspto-grants-2002_09
Patent number
US06455528B1

Reaction notes

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