1,1'-Carbonyldiimidazole → N-[5-[N-[3-(4-chlorophenyl)-3-(2-pyridyl)propyl]-N-methylamino]pentyl]-N'-[3-[3-(piperidinomethyl)phenoxy]propyl]urea

HRID 248954Notes

Reaction equation

HRID 248954 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][N:20]=2)[CH2:9][CH2:10][N:11]([CH3:18])[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][NH2:17])=[CH:4][CH:3]=1.[C:25](N1C=CN=C1)(N1C=CN=C1)=[O:26].[N:37]1([CH2:43][C:44]2[CH:45]=[C:46]([CH:52]=[CH:53][CH:54]=2)[O:47][CH2:48][CH2:49][CH2:50][NH2:51])[CH2:42][CH2:41][CH2:40][CH2:39][CH2:38]1>C(Cl)Cl>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][N:20]=2)[CH2:9][CH2:10][N:11]([CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][NH:17][C:25]([NH:51][CH2:50][CH2:49][CH2:48][O:47][C:46]2[CH:52]=[CH:53][CH:54]=[C:44]([CH2:43][N:37]3[CH2:42][CH2:41][CH2:40][CH2:39][CH2:38]3)[CH:45]=2)=[O:26])[CH3:18])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 682631,1'-CarbonyldiimidazoleHCID 102205613-(3-(Piperidin-1-ylmethyl)phenoxy)propan-1-amineHCID 19762500HCID 19762500, compound

Product 1

HCID 19762553N-[5-[N-[3-(4-chlorophenyl)-3-(2-pyridyl)propyl]-N-methylamino]pentyl]-N'-[3-[3-(piperidinomethyl)phenoxy]propyl]urea

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Preparation is effected analogously to Example 63, using 1.29 g (3.6 mmol) of N-[3-(4-chlorophenyl)-3-(2-pyridyl)propyl]-N-methyl-1,5-pentanediamine, an equimolar amount of 1,1'-carbonyldiimidazole and 1.04 g (4.2 mmol) of 3-[3-(piperidinomethyl)phenoxy]propaneamine 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 (+EI-80 eV): m/z (rel. int.[%])=619 ([M])+.,<1), 230 (17) 203 (100); IR (KBr): 1634 cm-1 (C≡0).

Workup

  1. customPreparation
  2. custompurified title compound in the form of an oil

Sources & evidence

ORD record
ord-c767768ef986444ea16e61436861b817
Source dataset
uspto-grants-1993_05
Patent number
US05212187

Reaction notes

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