Triethylamine → 1-[4-(4-Chlorobenzyl)-1-piperazinyl]-3-(4-phenacyl-1-piperazinyl)propane

HRID 4315Notes

Reaction equation

HRID 4315 reaction equation
[CH2:1]([N:10]1[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]1)[C:2]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)=[O:3].Cl[CH2:17][CH2:18][CH2:19][N:20]1[CH2:25][CH2:24][N:23]([CH2:26][C:27]2[CH:32]=[CH:31][C:30]([Cl:33])=[CH:29][CH:28]=2)[CH2:22][CH2:21]1.C(N(CC)CC)C>C(O)C>[Cl:33][C:30]1[CH:31]=[CH:32][C:27]([CH2:26][N:23]2[CH2:24][CH2:25][N:20]([CH2:19][CH2:18][CH2:17][N:13]3[CH2:14][CH2:15][N:10]([CH2:1][C:2]([C:4]4[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=4)=[O:3])[CH2:11][CH2:12]3)[CH2:21][CH2:22]2)=[CH:28][CH:29]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 47387141-Phenyl-2-(piperazin-1-yl)ethanoneHCID 133997271-[(4-Chlorophenyl)methyl]-4-(3-chloropropyl)piperazine

Product 1

HCID 140970431-[4-(4-Chlorobenzyl)-1-piperazinyl]-3-(4-phenacyl-1-piperazinyl)propaneYield 77.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 4.1 g of 1-phenacylpiperazine, 5.7 g of 1-chloro-3-[4-(4-chlorobenzyl)-1-piperazinyl]propane, 2.6 g of triethylamine and 35 ml of reagent ethanol was refluxed for 5 hours. The solvent was removed by rotary evaporation, 150 ml of water were added, and the mixture was extracted with ether (3×150 ml). The ether solution was evaporated to an oil, which was chromatographed on a silica column, the eluant being CH2Cl2 /CH3OH/ammonium hydroxide (45:5:1), to yield crude 1-[4-(4-chlorobenzyl)-1-piperazinyl]-3-(4-phenacyl-1-piperazinyl)propane (7.0 g, 50% of theory). This oil was dissolved in 200 ml of ether and precipitated with excess anhydrous hydrogen chloride. The precipitate was then dissolved in water and reprecipitated by addition of acetone to give 1-[4-(4-chlorobenzyl)-1-piperazinyl]-3-(4-phenacyl-1-piperazinyl)propane tetrahydrochloride monohydrate as a white crystalline product (m.p. 211°-218° C.).

Workup

  1. temperaturewas refluxed for 5 hours
  2. customThe solvent was removed by rotary evaporation, 150 ml of water
  3. additionwere added
  4. extractionthe mixture was extracted with ether (3×150 ml)
  5. customThe ether solution was evaporated to an oil, which
  6. customwas chromatographed on a silica column

Sources & evidence

ORD record
ord-9e8e1e68cd8c457689d598080df4296f
Source dataset
uspto-grants-1988_02
Patent number
US04725597

Reaction notes

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