1,1'-Carbonyldiimidazole → N-[2-[N-[3-(4-chlorophenyl)-3-(2-pyridyl)propyl]-N-methylamino]ethyl]-N'-[4-[3-(piperidinomethyl)phenoxy]butyl]urea

HRID 248953

Reaktionsgleichung

Reaktionsgleichung von HRID 248953
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][N:17]=2)[CH2:9][CH2:10][N:11]([CH3:15])[CH2:12][CH2:13][NH2:14])=[CH:4][CH:3]=1.[C:22](N1C=CN=C1)(N1C=CN=C1)=[O:23].[N:34]1([CH2:40][C:41]2[CH:42]=[C:43]([CH:50]=[CH:51][CH:52]=2)[O:44][CH2:45][CH2:46][CH2:47][CH2:48][NH2:49])[CH2:39][CH2:38][CH2:37][CH2:36][CH2:35]1>C(Cl)Cl>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][N:17]=2)[CH2:9][CH2:10][N:11]([CH2:12][CH2:13][NH:14][C:22]([NH:49][CH2:48][CH2:47][CH2:46][CH2:45][O:44][C:43]2[CH:50]=[CH:51][CH:52]=[C:41]([CH2:40][N:34]3[CH2:39][CH2:38][CH2:37][CH2:36][CH2:35]3)[CH:42]=2)=[O:23])[CH3:15])=[CH:4][CH:3]=1

Komponenten

5

Edukt 3

HCID 682631,1'-CarbonyldiimidazoleHCID 137906124-(3-Piperidinomethylphenoxy)butaneamineHCID 19762518N-[3-(4-chlorophenyl)-3-(2-pyridyl)propyl]-N-methyl-1,2-ethanediamine

Produkt 1

HCID 19762561N-[2-[N-[3-(4-chlorophenyl)-3-(2-pyridyl)propyl]-N-methylamino]ethyl]-N'-[4-[3-(piperidinomethyl)phenoxy]butyl]urea

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

Preparation is effected analogously to Example 63, using 0.8 g (2.6 mmol) of N-[3-(4-chlorophenyl)-3-(2-pyridyl)propyl]-N-methyl-1,2-ethanediamine, an equimolar amount of 1,1'-carbonyldiimidazole and 0.69 g (2.7 mmol) of 4-[3-(piperidinomethyl)phenoxy]butaneamine as starting materials. Working up by chromatography (eluant: methylene chloride) analogously to Example 63 yields the purified title compound in the form of an oil; MS (+FAB method): m/z (rel. int.[%])=592 ([M+H]+, 2), 230 (100); IR (KBr): 1632 cm-1 (C≡O). For analytical purposes a sample is converted into the O,O'-ditoluoyltartaric acid salt and recrystallised from ether/isopropanol; m.p.: from 124° C. with decomposition.

Aufarbeitung

  1. customPreparation
  2. custompurified title compound in the form of an oil
  3. customrecrystallised from ether/isopropanol
  4. customfrom 124° C.

Quellen und Nachweise

ORD-Eintrag
ord-78e34f70dec646ccb93539a69301168e
Quelldatensatz
uspto-grants-1993_05
Patentnummer
US05212187

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