Methyl iodide → 1-Methyl-3-(4-chlorophenyl)piperazine dihydrochloride

HRID 1165793Notes

Reaction equation

HRID 1165793 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[CH2:13][NH:12][CH2:11][CH2:10][NH:9]2)=[CH:4][CH:3]=1.[C:14]([O-])([O-])=O.[Na+].[Na+].IC>O>[ClH:1].[ClH:1].[CH3:14][N:12]1[CH2:11][CH2:10][NH:9][CH:8]([C:5]2[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=2)[CH2:13]1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 10340Sodium CarbonateHCID 38702732-(4-Chlorophenyl)piperazine2×

Product 1

HCID 137874451-Methyl-3-(4-chlorophenyl)piperazine dihydrochlorideYield 20.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 10 g (0.051 mol) of 2-(4-chlorophenyl)piperazine (comparison product CP 1 of Table IV below; M.p=124° C.) 10.80 g (0.102 mol) of Na2CO3, 7.24 g (0.051 mol) of ICH3 and 100 ml of water is heated under reflux for 6 hours. It is cooled, extraction is carried out with CHCl3 and the chloroform phase is washed with water and dried over MgSO4. It is filtered, the filtrate is evaporated to dryness, the evaporation residue is taken up with CH3OH and the mixture is acidified with a solution of hydrochloric acid in ethanol. It is evaporated to dryness; recrystallization of the evaporation residue from a methanol/ethyl acetate mixture (1:1 v/v) gives 3 g (yield: 20.8%) of CRL 41 202. M.p.inst. =200° C. (decomposition).

Workup

  1. temperatureis heated
  2. temperatureunder reflux for 6 hours
  3. temperatureIt is cooled
  4. extractionextraction
  5. washthe chloroform phase is washed with water
  6. dry with materialdried over MgSO4
  7. filtrationIt is filtered
  8. customthe filtrate is evaporated to dryness
  9. customIt is evaporated to dryness
  10. customrecrystallization of the evaporation residue from a methanol/ethyl acetate mixture (1:1 v/v)
  11. customgives 3 g (yield: 20.8%) of CRL 41 202

Sources & evidence

ORD record
ord-0035001b7ab742b683aee3c2b2de8108
Source dataset
uspto-grants-1990_03
Patent number
US04912110

Reaction notes

Loading…