Hydrochloric Acid → 1,3-Bis[4-(3-chlorobenzyl)-1-piperazinyl]propane dihydrochloride monohydrate

HRID 4318

Reaktionsgleichung

Reaktionsgleichung von HRID 4318
[Cl:1][C:2]1[CH:3]=[C:4]([CH:12]=[CH:13][CH:14]=1)[CH2:5][N:6]1[CH2:11][CH2:10][NH:9][CH2:8][CH2:7]1.Br[CH2:16][CH2:17][CH2:18][Cl:19].[CH2:20]([Cl:22])Cl.C[OH:24].[OH-].[NH4+:26].Cl>C(O)C.O.C(N(CC)CC)C>[OH2:24].[ClH:1].[ClH:19].[Cl:1][C:2]1[CH:3]=[C:4]([CH:12]=[CH:13][CH:14]=1)[CH2:5][N:6]1[CH2:7][CH2:8][N:9]([CH2:16][CH2:17][CH2:18][N:26]2[CH2:10][CH2:11][N:6]([CH2:5][C:4]3[CH:3]=[CH:2][CH:14]=[C:20]([Cl:22])[CH:12]=3)[CH2:7][CH2:8]2)[CH2:10][CH2:11]1

Komponenten

8

Edukt 4

HCID 313Hydrochloric AcidHCID 80061-Bromo-3-chloropropaneHCID 7647271-(3-Chlorobenzyl)piperazineHCID 21896990Dichloromethane methanol ammonium hydroxide

Produkt 1

HCID 201522391,3-Bis[4-(3-chlorobenzyl)-1-piperazinyl]propane dihydrochloride monohydrateAusbeute 68 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 702EthanolLösungsmittel2×HCID 962WaterLösungsmittelHCID 8471TriethylamineLösungsmittel

Versuchsvorschrift

A mixture of 6.3 g of 1-(3-chlorobenzyl)piperazine, 2.4 g of 1-bromo-3-chloropropane, 50 ml of reagent ethanol and 3.0 g of triethylamine was refluxed for 4 hours. Water (70 ml) was added, and the mixture was concentrated under vacuum to about 70 ml. The resulting aqueous mixture was extracted with ether (3×150 ml), and the extract was concentrated under vacuum to give a reddish-yellow oil. Chromatography of this oil on a silica column, the eluant being CH2Cl2 /CH3OH/ammonium hydroxide (45:5:1), resulted in an oil which was dissolved in 50 ml of ethanol. Hydrogen chloride-saturated ether was added to this solution until the mixture tested acidic to litmus. The resulting precipitate was filtered off, dried and weighed to yield 5.6 g (68% of theory) of 1,3-bis[4-(3-chlorobenzyl)-1-piperazinyl]propane dihydrochloride monohydrate. Recrystallization from water gave a white crystalline solid (m.p. 248°-257° C., with decomp.).

Aufarbeitung

  1. temperaturewas refluxed for 4 hours
  2. concentrationthe mixture was concentrated under vacuum to about 70 ml
  3. extractionThe resulting aqueous mixture was extracted with ether (3×150 ml)
  4. concentrationthe extract was concentrated under vacuum
  5. customto give a reddish-yellow oil
  6. customresulted in an oil which
  7. filtrationThe resulting precipitate was filtered off
  8. customdried

Quellen und Nachweise

ORD-Eintrag
ord-7341df2adb3541c79cb658048cb382de
Quelldatensatz
uspto-grants-1988_02
Patentnummer
US04725597

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