Triethylamine → 1-[(3,4-Dimethoxyphenyl)methyl]-4-(3,3-diphenylpropyl)piperazine

HRID 1076791Notes

Reaction equation

HRID 1076791 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.C(N(CC)CC)C.C(=O)([O-])[O-].[K+].[K+]>C1(C)C=CC=CC=1.CN(C)C=O>[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

7

Reactant 4

HCID 8471TriethylamineHCID 11430Potassium CarbonateHCID 81740Veratryl chlorideHCID 10356330N-3,3-Diphenylpropylpiperazine

Product 1

HCID 215378071-[(3,4-Dimethoxyphenyl)methyl]-4-(3,3-diphenylpropyl)piperazineYield 83.6%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6228DimethylformamideSolvent

Procedure

N-3,3-Diphenylpropylpiperazine in the amount of 2.8 g (0.01 mole), 1.87 g (0.01 mole) 9f 3,4-dimethoxybenzyl chloride, 0.5 g (0.005 mole) of triethylamine, 1.4 g (0.01 mole) of potassium carbonate, and 2 ml of dimethylformamide were mixed with 20 ml of toluene, and the resulting mixture was heated at the refluxing temperature for 2 hours. The reaction liquid was left to cool, washed by shaking with water, and the organic solvent layer was concentrated under reduced pressure to obtain 3.6 g (83.6% yield) of oily 1-(3,3-diphenylpropyl)-4-(3,4-dimethoxybenzyl)piperazine.

Workup

  1. temperaturethe resulting mixture was heated at the refluxing temperature for 2 hours
  2. customThe reaction liquid
  3. waitwas left
  4. temperatureto cool
  5. washwashed
  6. concentrationthe organic solvent layer was concentrated under reduced pressure

Sources & evidence

ORD record
ord-7778750b8ed64edcbfd72e0ba69523c8
Source dataset
uspto-grants-1976_05
Patent number
US03957790

Reaction notes

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