Tributylamine → 1-(3,3-Diphenylpropyl)-4-[(2,3,4-trimethoxyphenyl)methyl]piperazine

HRID 1076785

Reaction equation

HRID 1076785 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[C:31]([O:32][CH3:33])=[C:30]([O:34][CH3:35])[CH:29]=[CH:28][C:25]=1[CH2:26]Cl.C(N(CCCC)CCCC)CCC>C(OCCOCC)C>[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]([CH2:26][C:25]3[CH:28]=[CH:29][C:30]([O:34][CH3:35])=[C:31]([O:32][CH3:33])[C:24]=3[O:23][CH3:22])[CH2:14][CH2:15]2)[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

5

Reactant 3

HCID 7622TributylamineHCID 97491Toluene, alpha-chloro-2,3,4-trimethoxy-HCID 10356330N-3,3-Diphenylpropylpiperazine

Product 1

HCID 215378091-(3,3-Diphenylpropyl)-4-[(2,3,4-trimethoxyphenyl)methyl]piperazineYield 91.2%

Reagents, catalysts & solvents 1

HCID 12375Ethylene glycol diethyl etherSolvent

Procedure

N-3,3-Diphenylpropylpiperazine in the amount of 1.4 g (0.005 mole), 1.1 g (0.005 mole) of 2,3,4-trimethoxybenzyl chloride, and 0.93 g (0.005 mole) of tributylamine were dissolved in 10 ml of ethylene glycol diethyl ether, and the resulting solution was heated at the refluxing temperature for 2.5 hours. The reaction liquid was left to cool, and filtered, and concentration of the filtrate under reduced pressure produced 2.1 g of oily 1-(3,3-diphenylpropyl)-4-(2,3,4-trimethoxybenzyl)piperazine (91.2% yield).

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. filtrationfiltered

Sources & evidence

ORD record
ord-1a452d457cd349aaa31e2f8de88323f2
Source dataset
uspto-grants-1976_05
Patent number
US03957790

Linked notes

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