HCID 14479498, compound → 1,4-Dibenzyl-2-(chloromethyl)piperazine

HRID 1031570Notes

Reaction equation

HRID 1031570 reaction equation
[ClH:1].Cl.O[CH2:4][CH:5]1[CH2:10][N:9]([CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH2:8][CH2:7][N:6]1[CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>S(Cl)(Cl)=O>[Cl:1][CH2:4][CH:5]1[CH2:10][N:9]([CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH2:8][CH2:7][N:6]1[CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

3

Reactant 1

HCID 14479498HCID 14479498, compound

Product 1

HCID 106631191,4-Dibenzyl-2-(chloromethyl)piperazineYield 99.4%

Reagents, catalysts & solvents 1

HCID 24386Thionyl ChlorideSolvent

Procedure

A suspension of 23 g (62.3 mmol) of 2-hydroxymethyl-1,4-di-phenylmethyl piperazine, dihydrochloride in 79 ml thionyl chloride was heated 4 hours under reflux. The solution was cooled and excess thionyl chloride was evaporated under reduced pressure. The residue was crystallized in ethanol, dried with acetone to yield 19.5 g of title compound dihydrochloride M.P. 234° C. dec. A suspension of this dihydrochloride in 130 ml 1N aqueous sodium hydroxyde was stirred with 75 ml dichloromethane, the aqueous layer back washed three times with 75 ml dichloromethane. The organic layers were collected and dried over magnesium sulfate to give after evaporation 15.44 g (78%) of title compound.

Workup

  1. temperaturewas heated 4 hours
  2. temperatureunder reflux
  3. temperatureThe solution was cooled
  4. customexcess thionyl chloride was evaporated under reduced pressure
  5. customThe residue was crystallized in ethanol
  6. dry with materialdried with acetone

Sources & evidence

ORD record
ord-35b3150ae5d645eeafc445d9f892d212
Source dataset
uspto-grants-1990_09
Patent number
US04954507

Reaction notes

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