Triethylamine → 1-{3-[4-[3-(4-Chlorophenyl)propyl]piperazin-1-yl]-propyl}-3-n-hexylurea dihydrochloride

HRID 1380198Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1380198
[Cl:1][CH2:2][CH2:3][CH2:4][NH:5][C:6]([NH:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14])=[O:7].[Cl:15][C:16]1[CH:21]=[CH:20][C:19]([CH2:22][CH2:23][CH2:24][N:25]2[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]2)=[CH:18][CH:17]=1.C(N(CC)CC)C>CCOCC>[ClH:1].[ClH:15].[Cl:15][C:16]1[CH:21]=[CH:20][C:19]([CH2:22][CH2:23][CH2:24][N:25]2[CH2:26][CH2:27][N:28]([CH2:2][CH2:3][CH2:4][NH:5][C:6]([NH:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14])=[O:7])[CH2:29][CH2:30]2)=[CH:18][CH:17]=1

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 1628731-(3-(4-Chlorophenyl)propyl)piperazineHCID 136067321-(3-Chloropropyl)-3-n-hexylurea

Produkt 1

HCID 136067251-{3-[4-[3-(4-Chlorophenyl)propyl]piperazin-1-yl]-propyl}-3-n-hexylurea dihydrochlorideAusbeute 64,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3283Diethyl EtherLösungsmittel

Versuchsvorschrift

A mixture of 1-(3-chloropropyl)-3-n-hexylurea (2.21 g; 10 mmole), 1-[3-(4-chlorophenyl)propyl]piperazine (2.39 g; 10 mmole), triethylamine (1.01 g; 10 mmole) and alcohol (25 ml) was refluxed for 18 hours. The cooled reaction mixture was diluted with ether and washed with water, dried (sodium sulfate) and concentrated in vacuo. The resulting yellow viscous oil was purified on a silica gel column (methylene chloride/methanol; 93:7) and precipitated with ethereal hydrochloric acid to provide the title compound (1.6 g; 38% yield) as colorless crystals, m.p. 213°-216° C.

Aufarbeitung

  1. temperaturewas refluxed for 18 hours
  2. customThe cooled reaction mixture
  3. washwashed with water
  4. dry with materialdried (sodium sulfate)
  5. concentrationconcentrated in vacuo
  6. customThe resulting yellow viscous oil was purified on a silica gel column (methylene chloride/methanol; 93:7)
  7. customprecipitated with ethereal hydrochloric acid

Quellen und Nachweise

ORD-Eintrag
ord-f311854efdbd49e0a98586968b38e346
Quelldatensatz
uspto-grants-1986_04
Patentnummer
US04579947

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