Triethylamine → 1-Cinnamyl-4-(3-chloropropyl)piperazine dihydrochloride

HRID 2290896Notes

Reaction equation

HRID 2290896 reaction equation
[CH2:1](Br)[CH:2]=[CH:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.O.Cl.Cl.[Cl:14][CH2:15][CH2:16][CH2:17][N:18]1[CH2:23][CH2:22][NH:21][CH2:20][CH2:19]1.[Cl:24]CCCN1CCNCC1.Cl.Cl.C(N(CC)CC)C>C(O)C>[ClH:14].[ClH:24].[CH2:1]([N:21]1[CH2:22][CH2:23][N:18]([CH2:17][CH2:16][CH2:15][Cl:14])[CH2:19][CH2:20]1)[CH:2]=[CH:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 98116BromomethylstyreneHCID 131714940Bis(1-(3-chloropropyl)piperazine);hydrate;tetrahydrochloride

Product 1

HCID 704154971-Cinnamyl-4-(3-chloropropyl)piperazine dihydrochlorideYield 278.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

6.0 g of cinnamyl bromide were added to a mixture of 7.4 g of 1-(3-chloropropyl)piperazine dihydrochloride hemihydrate, 6.1 g of triethylamine and 100 ml of reagent ethanol. The mixture was refluxed for 4 hours and then stirred overnight. After removal of the solvent in vacuo, water was added to the residue. The product was then extracted with ether and the extract was dried (magnesium sulfate) and concentrated. The resulting oil was chromatographed on silica gel (methylene chloride/methanol: 9/1) and precipitated with ethereal hydrochloric acid to give 7.4 g (70% of theory) of 1-cinnamyl-4-(3-chloropropyl)piperazine dihydrochloride.

Workup

  1. temperatureThe mixture was refluxed for 4 hours
  2. customAfter removal of the solvent in vacuo, water
  3. additionwas added to the residue
  4. extractionThe product was then extracted with ether
  5. dry with materialthe extract was dried (magnesium sulfate)
  6. concentrationconcentrated
  7. customThe resulting oil was chromatographed on silica gel (methylene chloride/methanol: 9/1)
  8. customprecipitated with ethereal hydrochloric acid

Sources & evidence

ORD record
ord-4f7f1dee9e7649e88f58a158fbc50bd5
Source dataset
uspto-grants-1986_10
Patent number
US04618677

Reaction notes

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