Potassium Hydroxide → 1,4-Dibenzyl-2-(chloromethyl)piperazine

HRID 2165599Notes

Reaction equation

HRID 2165599 reaction equation
S(Cl)([Cl:3])=O.[C:5]1([CH2:11][N:12]2[CH2:17][CH2:16][N:15]([CH2:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[CH2:14][CH:13]2[CH2:25]O)[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.[OH-].[K+]>C(Cl)(Cl)(Cl)Cl.O>[Cl:3][CH2:25][CH:13]1[CH2:14][N:15]([CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH2:16][CH2:17][N:12]1[CH2:11][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1

Participants

6

Reactant 3

HCID 14797Potassium HydroxideHCID 24386Thionyl ChlorideHCID 10827800(1,4-Dibenzylpiperazin-2-yl)methanol

Product 1

HCID 106631191,4-Dibenzyl-2-(chloromethyl)piperazine

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 5943Carbon TetrachlorideSolvent2×

Procedure

To a solution of 10.1 ml of thionyl chloride in 50 ml of carbon tetrachloride was added, with stirring, a solution of 22.15 g of 1,4-bis(phenylmethyl)-2-piperazinemethanol in 120 ml of carbon tetrachloride. This mixture was stirred in an oil bath at 70° C. for one hour, then cooled in an ice bath and a solution of 17.1 g of potassium hydroxide in 50 ml of water was added. The mixture was extracted several times with dichloromethane. The extracts were combined, filtered through hydrous magnesium silicate and evaporated. The residual gum was dissolved in warm heptane, filtered and evaporated to an oil which crystallized on standing, giving 17.94 g of 2-chloromethyl-1,4-bis(phenylmethyl)piperazine, mp 54°-56° C.

Workup

  1. stirringThis mixture was stirred in an oil bath at 70° C. for one hour
  2. temperaturecooled in an ice bath
  3. extractionThe mixture was extracted several times with dichloromethane
  4. filtrationfiltered through hydrous magnesium silicate
  5. customevaporated
  6. dissolutionThe residual gum was dissolved in warm heptane
  7. filtrationfiltered
  8. customevaporated to an oil which
  9. customcrystallized

Sources & evidence

ORD record
ord-8d78857d7fcb41f8af469c0d9ad77163
Source dataset
uspto-grants-1990_07
Patent number
US04940710

Reaction notes

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