Ethanol → 1-{3-{4-[3-(4-Chlorophenyl)propyl]piperazin-1-yl}propyl}3-(4-cyanophenyl)urea

HRID 1380202Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1380202
Cl[CH2:2][CH2:3][CH2:4][NH:5][C:6]([NH:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]#[N:16])=[CH:11][CH:10]=1)=[O:7].[Cl:17][C:18]1[CH:23]=[CH:22][C:21]([CH2:24][CH2:25][CH2:26][N:27]2[CH2:32][CH2:31][NH:30][CH2:29][CH2:28]2)=[CH:20][CH:19]=1.C(N(CC)CC)C.C(O)C>CCOCC>[Cl:17][C:18]1[CH:23]=[CH:22][C:21]([CH2:24][CH2:25][CH2:26][N:27]2[CH2:28][CH2:29][N:30]([CH2:2][CH2:3][CH2:4][NH:5][C:6]([NH:8][C:9]3[CH:14]=[CH:13][C:12]([C:15]#[N:16])=[CH:11][CH:10]=3)=[O:7])[CH2:31][CH2:32]2)=[CH:20][CH:19]=1

Komponenten

6

Edukt 4

HCID 702EthanolHCID 8471TriethylamineHCID 1628731-(3-(4-Chlorophenyl)propyl)piperazineHCID 136067331-(3-Chloropropyl)-3-(4-cyanophenyl)urea

Produkt 1

HCID 136067281-{3-{4-[3-(4-Chlorophenyl)propyl]piperazin-1-yl}propyl}3-(4-cyanophenyl)ureaAusbeute 42 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3283Diethyl EtherLösungsmittel

Versuchsvorschrift

A mixture of 1-(3-chloropropyl)-3-(4-cyanophenyl)urea (3.57 g; 15 mmole), 1-[3-(4-chlorophenyl)propyl]piperazine (3.58 g; 15 mmole), triethylamine (1.52 g; 15 mmole), and ethanol (100 ml) was refluxed for 35 hours. The solvent was removed in vacuo and water added to the residue. The product was extracted with ether, dried, and concentrated in vacuo. The resulting reddish-yellow oil was purified on a silica gel column (methylene chloride/methanol 9:1) to give the product as a free base (2.8 g; 42% yield). The product was dissolved in ether and precipitated with ethereal hydrochloric acid to provide, after recrystallization from water, the title compound as colorless crystals, m.p. 219°-221° C.

Aufarbeitung

  1. temperaturewas refluxed for 35 hours
  2. customThe solvent was removed in vacuo and water
  3. additionadded to the residue
  4. extractionThe product was extracted with ether
  5. customdried
  6. concentrationconcentrated in vacuo
  7. customThe resulting reddish-yellow oil was purified on a silica gel column (methylene chloride/methanol 9:1)
  8. customto give the product as a free base (2.8 g; 42% yield)
  9. customprecipitated with ethereal hydrochloric acid
  10. customto provide
  11. customafter recrystallization from water

Quellen und Nachweise

ORD-Eintrag
ord-ce57af3d83a3486687082a4cdfe226f2
Quelldatensatz
uspto-grants-1986_04
Patentnummer
US04579947

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