Triethylamine → HCID 21537802, compound

HRID 1076782Notes

Reaction equation

HRID 1076782 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:14]1([CH:20]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH2:21][CH2:22][Cl:23])[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.C(N(CC)CC)C>C1(C)C(C)=CC=CC=1>[ClH:23].[ClH:23].[C:14]1([CH:20]([C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=2)[CH2:21][CH2:22][N:11]2[CH2:12][CH2:13][N:8]([CH2:1][C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)[CH2:9][CH2:10]2)[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 759941-BenzylpiperazineHCID 1901351,1'-(3-Chloropropane-1,1-diyl)dibenzene

Product 1

HCID 21537802HCID 21537802, compoundYield 170%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

To a solution containing 17.62 g (0.1 mole) of N-benzyl-piperazine in 100 ml of xylene were added 23.05 g (0.1 mole) of 3,3-diphenylpropyl chloride and 10.1 g (0.1 mole) of triethylamine, and the resulting solution was heated at the refluxing temperature for 2.5 hours. The reaction liquid was left to cool, and the triethylamine hydrochloride which precipitated was filtered out. Then, dry hydrogen chloride gas was passed through this solution, while the solution was cooled so as to precipitate 1-(3,3-diphenyl-propyl)-4-benzylpiperazine dihydrochloride. The crystals were recovered by filtration, and recrystallized from an ethanol and ether mixed solvent to obtain 37.7 g of pure crystals (85.0% yield) with a melting point of 187°- 188°C.

Workup

  1. temperaturethe resulting solution was heated at the refluxing temperature for 2.5 hours
  2. customThe reaction liquid
  3. waitwas left
  4. temperatureto cool
  5. customthe triethylamine hydrochloride which precipitated
  6. filtrationwas filtered out
  7. temperaturewas cooled so as
  8. customto precipitate 1-(3,3-diphenyl-propyl)-4-benzylpiperazine dihydrochloride
  9. filtrationThe crystals were recovered by filtration
  10. customrecrystallized from an ethanol and ether mixed solvent

Sources & evidence

ORD record
ord-c79cec6ad80542f59cba25f58b37230e
Source dataset
uspto-grants-1976_05
Patent number
US03957790

Reaction notes

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