Hydrochloric Acid → 1-(3,3-Diphenylpropyl)-4(3,4-dimethoxybenzyl)piperazine dihydrochloride

HRID 1076786Notes

Reaction equation

HRID 1076786 reaction equation
[C:1]1([CH:7]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH2:8][CH2:9][N:10]2[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:22][O:23][C:24]1[CH:25]=[C:26]([CH:29]=[CH:30][C:31]=1[O:32][CH3:33])[CH2:27][Cl:28].[ClH:34]>C(C(C)=O)C>[ClH:28].[ClH:34].[C:16]1([CH:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[CH2:8][CH2:9][N:10]2[CH2:11][CH2:12][N:13]([CH2:27][C:26]3[CH:29]=[CH:30][C:31]([O:32][CH3:33])=[C:24]([O:23][CH3:22])[CH:25]=3)[CH2:14][CH2:15]2)[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 81740Veratryl chlorideHCID 10356330N-3,3-Diphenylpropylpiperazine

Product 1

HCID 215378181-(3,3-Diphenylpropyl)-4(3,4-dimethoxybenzyl)piperazine dihydrochlorideYield 87.4%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

N-3,3-Diphenylpropylpiperazine in the amount of 2.8 g (0.01 mole) and 1.87 g (0.01 mole) of 3,4-dimethoxybenzyl chloride were dissolved in 20 ml of methyl ethyl ketone, and the resulting solution was heated at the refluxing temperature for 7.5 hours. After the reaction liquid was left to cool, dry hydrogen chloride gas was passed through the liquid while cooling the liquid to precipitate 1-(3,3-diphenylpropyl)-4-(3,4-dimethoxybenzyl)piperazine dihydrochloride. The crystals of this salt were recrystallized from an ethanol and ether mixed solvent to obtain 4.4 g (87.4% yield) of pure crystals with a melting point of 184°C.

Workup

  1. temperaturethe resulting solution was heated at the refluxing temperature for 7.5 hours
  2. customAfter the reaction liquid
  3. waitwas left
  4. temperatureto cool
  5. temperaturewhile cooling the liquid
  6. customto precipitate 1-(3,3-diphenylpropyl)-4-(3,4-dimethoxybenzyl)piperazine dihydrochloride
  7. customThe crystals of this salt were recrystallized from an ethanol and ether mixed solvent

Sources & evidence

ORD record
ord-4c441f7d0045495d8deef7053b50f7a1
Source dataset
uspto-grants-1976_05
Patent number
US03957790

Reaction notes

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