Water → 1-(3-Chlorophenyl)-4-(3-chloropropyl)-piperazine

HRID 1414006Notes

Reaction equation

HRID 1414006 reaction equation
[OH-].[Na+].O.Cl.[Cl:5][C:6]1[CH:7]=[C:8]([N:12]2[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]2)[CH:9]=[CH:10][CH:11]=1.Br[CH2:19][CH2:20][CH2:21][Cl:22]>CC(C)=O>[Cl:5][C:6]1[CH:7]=[C:8]([N:12]2[CH2:17][CH2:16][N:15]([CH2:19][CH2:20][CH2:21][Cl:22])[CH2:14][CH2:13]2)[CH:9]=[CH:10][CH:11]=1

Participants

6

Reactant 4

HCID 962WaterHCID 80061-Bromo-3-chloropropaneHCID 14798Sodium HydroxideHCID 256811-(3-Chlorophenyl)piperazine monohydrochloride

Product 1

HCID 1014441-(3-Chlorophenyl)-4-(3-chloropropyl)-piperazineYield 9%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution fo 7.36 g. (0.184 mole) of sodium hydroxide in 75 ml. of water and 75 ml. of acetone there is added 17.16 g. (0.074 mole) of 1-(3-chlorophenyl)piperazine hydrochloride and 11.59 g. (0.074 mole) of 1-bromo-3-chloropropane, and the resulting mixture is stirred at 27° for 18 hrs. The organic layer is then separated and concentrated to an oil under reduced pressure. The oil is treated with hot (85°) 6 N HCl until solution is complete, and the resulting solution is filtered and stored at 5° for 18 hrs. The precipitate which forms is collected on a filter to afford 17.52 g. (87%) of the hydrochloride salt of the product, m.p. 198°-200°. Concentration of the mother liquor under reduced pressure and recrystallization of the residue from water affords an additional 1.82 g (9%) of product, m.p. 196°-198°.

Workup

  1. customThe organic layer is then separated
  2. concentrationconcentrated to an oil under reduced pressure
  3. additionThe oil is treated with hot (85°) 6 N HCl until solution
  4. filtrationthe resulting solution is filtered
  5. customThe precipitate which forms is collected on
  6. filtrationa filter
  7. customto afford 17.52 g
  8. customConcentration of the mother liquor under reduced pressure and recrystallization of the residue from water

Sources & evidence

ORD record
ord-c7af2029361c420c8a72a17142596603
Source dataset
uspto-grants-1981_02
Patent number
US04252806

Reaction notes

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