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

HRID 248957Notes

Reaction equation

HRID 248957 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][N:19]=2)[CH2:9][CH2:10][N:11]([CH3:17])[CH2:12][CH2:13][CH2:14][CH2:15][NH2:16])=[CH:4][CH:3]=1.[C:24](N1C=CN=C1)(N1C=CN=C1)=[O:25].[N:36]1([CH2:42][C:43]2[CH:44]=[C:45]([CH:51]=[CH:52][CH:53]=2)[O:46][CH2:47][CH2:48][CH2:49][NH2:50])[CH2:41][CH2:40][CH2:39][CH2:38][CH2:37]1>C(OCC)(=O)C.CO>[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][N:19]=2)[CH2:9][CH2:10][N:11]([CH2:12][CH2:13][CH2:14][CH2:15][NH:16][C:24]([NH:50][CH2:49][CH2:48][CH2:47][O:46][C:45]2[CH:51]=[CH:52][CH:53]=[C:43]([CH2:42][N:36]3[CH2:41][CH2:40][CH2:39][CH2:38][CH2:37]3)[CH:44]=2)=[O:25])[CH3:17])=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 682631,1'-CarbonyldiimidazoleHCID 102205613-(3-(Piperidin-1-ylmethyl)phenoxy)propan-1-amineHCID 19762522HCID 19762522, compound

Product 1

HCID 10077111N-[4-[N-[3-(4-fluorophenyl)-3-(2-pyridyl)propyl]-N-methylamino]butyl]-N'-[3-[3-(piperidinomethyl)phenoxy]propyl]urea

Reagents, catalysts & solvents 1

HCID 21584119Ethylacetate methanolSolvent

Procedure

Preparation is effected analogously to Example 63, using 0.7 g (2.2 mmol) of N-[3-(4-fluorophenyl)-3-(2-pyridyl)propyl]-N-methyl-1,4-butanediamine, an equimolar amount of 1,1'-carbonyldiimidazole and 0.6 g (2.4 mmol) of 3-[3-(piperidinomethyl)phenoxy]propaneamine as starting materials. Working up by chromatography (eluant: ethyl acetate/methanol 95+5) analogously to Example 63 yields the purified title compound in the form of an oil; MS (+FAB method): m/z (rel. int.[%])=590 ([M+H]+ 17), 214 (100); IR (KBr): 1631 cm-1 (C=O).

Workup

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

Sources & evidence

ORD record
ord-2b11fdd1d35e42d79acd2d3875e4c70a
Source dataset
uspto-grants-1993_05
Patent number
US05212187

Reaction notes

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