Triethylamine → 1-{3-[4-(4-Chlorobenzyl)piperazin-1-yl]propyl}-3-allylurea dihydrochloride

HRID 543190

Reaktionsgleichung

Reaktionsgleichung von HRID 543190
C(N(CC)CC)C.[ClH:8].Cl.Cl.[NH2:11][CH2:12][CH2:13][CH2:14][N:15]1[CH2:20][CH2:19][N:18]([CH2:21][C:22]2[CH:27]=[CH:26][C:25]([Cl:28])=[CH:24][CH:23]=2)[CH2:17][CH2:16]1.[CH2:29]([N:32]=[C:33]=[O:34])[CH:30]=[CH2:31]>C(Cl)Cl>[ClH:28].[ClH:8].[Cl:28][C:25]1[CH:24]=[CH:23][C:22]([CH2:21][N:18]2[CH2:19][CH2:20][N:15]([CH2:14][CH2:13][CH2:12][NH:11][C:33]([NH:32][CH2:29][CH:30]=[CH2:31])=[O:34])[CH2:16][CH2:17]2)=[CH:27][CH:26]=1

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 15123Allyl isocyanateHCID 202057391-(3-Aminopropyl)-4-(4-chlorobenzyl)piperazine trihydrochloride

Produkt 1

HCID 136066961-{3-[4-(4-Chlorobenzyl)piperazin-1-yl]propyl}-3-allylurea dihydrochlorideAusbeute 49,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

A solution of triethylamine (2.0 g; 20 mmole) in methylene chloride was added dropwise to a mixture of 1-(3-amino-propyl)-4-(4-chlorobenzyl)piperazine trihydrochloride (7.54 g; 20 mmole) and allyl isocyanate (1.66 g; 20 mmole) in methylene chloride. After the addition was completed the mixture was washed with water and the solvent removed. The resulting orange oil was purified on a silica gel column (methylene chloride/methanol; 9:1), precipitated with ethereal hydrochloric acid, and recrystallized from ethanol/water to provide the title compound (2.1 g; 25% yield) as colorless crystals, m.p. 232°-234° C.

Aufarbeitung

  1. additionAfter the addition
  2. washwas washed with water
  3. customthe solvent removed
  4. customThe resulting orange oil was purified on a silica gel column (methylene chloride/methanol; 9:1)
  5. customprecipitated with ethereal hydrochloric acid
  6. customrecrystallized from ethanol/water

Quellen und Nachweise

ORD-Eintrag
ord-30b36e18d315416f89acb89c29e0e57d
Quelldatensatz
uspto-grants-1987_04
Patentnummer
US04661481

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