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

HRID 248958Notes

Reaction equation

HRID 248958 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][N:18]=2)[CH2:9][CH2:10][N:11]([CH3:16])[CH2:12][CH2:13][CH2:14][NH2:15])=[CH:4][CH:3]=1.[C:23](N1C=CN=C1)(N1C=CN=C1)=[O:24].[N:35]1([CH2:41][C:42]2[CH:43]=[C:44]([CH:50]=[CH:51][CH:52]=2)[O:45][CH2:46][CH2:47][CH2:48][NH2:49])[CH2:40][CH2:39][CH2:38][CH2:37][CH2:36]1>C(OCC)(=O)C.CO>[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][N:18]=2)[CH2:9][CH2:10][N:11]([CH2:12][CH2:13][CH2:14][NH:15][C:23]([NH:49][CH2:48][CH2:47][CH2:46][O:45][C:44]2[CH:50]=[CH:51][CH:52]=[C:42]([CH2:41][N:35]3[CH2:40][CH2:39][CH2:38][CH2:37][CH2:36]3)[CH:43]=2)=[O:24])[CH3:16])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 682631,1'-CarbonyldiimidazoleHCID 102205613-(3-(Piperidin-1-ylmethyl)phenoxy)propan-1-amineHCID 19762608N-[3-(4-fluorophenyl)-3-(2-pyridyl)propyl]-N-methyl-1,3-propanediamine

Product 1

HCID 11757861N-[3-[N-[3-(4-fluorophenyl)-3-(2-pyridyl)propyl]-N-methylamino]propyl]-N'-[3-[3-(piperidinomethyl)phenoxy]propyl]urea

Reagents, catalysts & solvents 1

HCID 21584119Ethylacetate methanolSolvent

Procedure

Preparation is effected analogously to Example 63, using 0.78 g (2.6 mmol) of N-[3-(4-fluorophenyl)-3-(2-pyridyl)propyl]-N-methyl-1,3-propanediamine, an equimolar amount of 1,1'-carbonyldiimidazole and 0.65 g (2.6 mmol) of 3-[3-(piperidinomethyl)phenoxy]propaneamine as starting materials. Working up by chromatography (eluant: ethyl acetate/methanol 9+1) analogously to Example 63 yields the purified title compound in the form of an oil; MS (+FAB method): m/z (rel. int.[%])=576 ([M+H]+,7), 214 (100); IR (KBr): 1649 cm-1 (C=O). For analytical purposes a sample is converted into the maleic acid salt and recrystallised from ether/ethanol; m.p.: 65°-67° C.

Workup

  1. customPreparation
  2. custompurified title compound in the form of an oil
  3. customrecrystallised from ether/ethanol

Sources & evidence

ORD record
ord-32f8b6089d854705b203ac86b29cf119
Source dataset
uspto-grants-1993_05
Patent number
US05212187

Reaction notes

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