1-Bromo-3-chloropropane → 1,3-Bis[4-(1-phenylethyl)-1-piperazinyl]propane tetrahydrochloride

HRID 4317Notes

Reaction equation

HRID 4317 reaction equation
[C:1]1([CH:7]([N:9]2[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]2)[CH3:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Br[CH2:16][CH2:17][CH2:18][Cl:19]>C(O)C>[ClH:19].[ClH:19].[ClH:19].[ClH:19].[C:1]1([CH:7]([N:9]2[CH2:10][CH2:11][N:12]([CH2:16][CH2:17][CH2:18][N:12]3[CH2:13][CH2:14][N:9]([CH:7]([C:1]4[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=4)[CH3:8])[CH2:10][CH2:11]3)[CH2:13][CH2:14]2)[CH3:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 80061-Bromo-3-chloropropaneHCID 27371341-(1-Phenylethyl)piperazine

Product 1

HCID 201522201,3-Bis[4-(1-phenylethyl)-1-piperazinyl]propane tetrahydrochlorideYield 211.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 7.6 g of 1-(1-phenylethyl)piperazine, 3.2 g of 1-bromo-3-chloropropane and 50 ml of reagent ethanol was refluxed for 5 hours. The solvent was then removed under vacuum, 75 ml of water were added, and the mixture was extracted with ether (3×150 ml). The ether extract was evaporated to an oil and chromatographed on silica, the eluant being CH2Cl2 /CH3OH/ammonium hydroxide (45:5:1). The resulting yellow oil was dissolved in 150 ml of ether and precipitated with excess anhydrous hydrogen chloride to yield 6.1 g (51% of theory) of 1,3-bis[4-(1-phenylethyl) -1-piperazinyl]propane tetrahydrochloride. The product was recrystallized from ethanol/water to yield a white crystalline solid (m.p. 236°-246° C., with decomp.).

Workup

  1. temperaturewas refluxed for 5 hours
  2. customThe solvent was then removed under vacuum, 75 ml of water
  3. additionwere added
  4. extractionthe mixture was extracted with ether (3×150 ml)
  5. extractionThe ether extract
  6. customwas evaporated to an oil
  7. customchromatographed on silica
  8. dissolutionThe resulting yellow oil was dissolved in 150 ml of ether
  9. customprecipitated with excess anhydrous hydrogen chloride

Sources & evidence

ORD record
ord-17ee4450157049288fbf93d876e000e4
Source dataset
uspto-grants-1988_02
Patent number
US04725597

Reaction notes

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