HCID 791403, compound → HCID 21331819, compound

HRID 1390975Notes

Reaction equation

HRID 1390975 reaction equation
[C:1]1([CH3:23])[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[N:7]1[CH2:12][CH2:11][N:10]([CH2:13][C:14]2[CH:19]=[CH:18][C:17]([N+:20]([O-])=O)=[CH:16][CH:15]=2)[CH2:9][CH2:8]1>CCOCC.[Cl-].[Cl-].[Cl-].[Ti+3]>[C:1]1([CH3:23])[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[N:7]1[CH2:8][CH2:9][N:10]([CH2:13][C:14]2[CH:15]=[CH:16][C:17]([NH2:20])=[CH:18][CH:19]=2)[CH2:11][CH2:12]1

Participants

4

Reactant 1

HCID 791403HCID 791403, compound

Product 1

HCID 21331819HCID 21331819, compoundYield 46.3%

Reagents, catalysts & solvents 2

HCID 10313229titanium(III) trichlorideCatalystHCID 3283Diethyl EtherSolvent

Procedure

To a suspension of 4-(o-tolyl)-1-(p-nitrobenzyl)piperazine (3.11 g, 0.01 M) in 30 ml of ether is added dropwise 30 ml of titanium trichloride (20% aqueous solution). The resulting mixture is stirred at room temperature for one hour. This is then quenched into cold water, made strongly basic with aqueous 10% ammonium hydroxide solution and extracted with methylene chloride. The methylene chloride solution is washed with water, dried over anhydrous sodium sulfate and concentrated to an oil. This is purified by column chromatography on silica gel to afford 1.3 g (46%) of 1-(o-tolyl)-4-[(4-aminophenyl)methyl]piperazine as an oil.

Workup

  1. customThis is then quenched into cold water
  2. extractionextracted with methylene chloride
  3. washThe methylene chloride solution is washed with water
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated to an oil
  6. customThis is purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-abb3ac0cd933431d811bc52374dd22d4
Source dataset
uspto-grants-1979_02
Patent number
US04140775

Reaction notes

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