1-(2-Methoxyphenyl)piperazine → 2-[4-(2-Methoxyphenyl)piperazin-1-yl]-N-(triphenylmethyl)ethanamine

HRID 37191

Reaction equation

HRID 37191 reaction equation
Br[CH2:2][CH2:3][NH:4][C:5]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.[CH3:24][O:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=1[N:32]1[CH2:37][CH2:36][NH:35][CH2:34][CH2:33]1.C(=O)([O-])[O-].[K+].[K+].[I-].[Na+]>CN(C)C=O.C(#N)C>[CH3:24][O:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=1[N:32]1[CH2:37][CH2:36][N:35]([CH2:2][CH2:3][NH:4][C:5]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=2)[CH2:34][CH2:33]1

Participants

7

Reactant 4

HCID 13461-(2-Methoxyphenyl)piperazineHCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 15718287(2-Bromoethyl)tritylamine

Product 1

HCID 157182882-[4-(2-Methoxyphenyl)piperazin-1-yl]-N-(triphenylmethyl)ethanamineYield 70.9%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6342AcetonitrileSolvent

Procedure

10 g (0.273 mol) of 2-bromo-N-(triphenylmethyl)ethanamine, 200 ml of acetonitrile, 5.15 g (0.0273 mol) of 1-(2-methoxyphenyl)piperazine, 5.6 g of anhydrous potassium carbonate, a few grains of sodium iodide and 1 ml of dimethylformamide are introduced into a 500 ml round-bottomed flask equipped with a reflux condenser and placed under nitrogen. The mixture is heated at reflux for 15 h, the solvents are evaporated, water and dichloromethane are added, the organic phase is separated, washed with water, dried over sodium sulphate and the solvent is evaporated under reduced pressure. A viscous oil is obtained which is purified by chromatography on a column of silica gel, the eluent being a mixture of ethyl acetate and dichloromethane. There are isolated 9.24 g of product which is used as is in the following stage.

Workup

  1. customequipped with a reflux condenser
  2. temperatureThe mixture is heated
  3. temperatureat reflux for 15 h
  4. customthe solvents are evaporated
  5. additionwater and dichloromethane are added
  6. customthe organic phase is separated
  7. washwashed with water
  8. dry with materialdried over sodium sulphate
  9. customthe solvent is evaporated under reduced pressure
  10. customA viscous oil is obtained which
  11. customis purified by chromatography on a column of silica gel
  12. additionthe eluent being a mixture of ethyl acetate and dichloromethane

Sources & evidence

ORD record
ord-4daa1fcf7cfe48e6859b359d484a1e7b
Source dataset
uspto-grants-1995_05
Patent number
US05420130

Linked notes

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