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

HRID 248961Notes

Reaction equation

HRID 248961 reaction equation
[CH3:1][N:2]([CH2:7][CH2:8][CH:9]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][N:11]=1)[CH2:3][CH2:4][CH2:5][NH2:6].[C:22](N1C=CN=C1)(N1C=CN=C1)=[O:23].[N:34]1([CH2:40][C:41]2[CH:42]=[C:43]([CH:49]=[CH:50][CH:51]=2)[O:44][CH2:45][CH2:46][CH2:47][NH2:48])[CH2:39][CH2:38][CH2:37][CH2:36][CH2:35]1>C(OCC)(=O)C.CO>[C:16]1([CH:9]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][N:11]=2)[CH2:8][CH2:7][N:2]([CH2:3][CH2:4][CH2:5][NH:6][C:22]([NH:48][CH2:47][CH2:46][CH2:45][O:44][C:43]2[CH:49]=[CH:50][CH:51]=[C:41]([CH2:40][N:34]3[CH2:39][CH2:38][CH2:37][CH2:36][CH2:35]3)[CH:42]=2)=[O:23])[CH3:1])[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

5

Reactant 3

HCID 682631,1'-CarbonyldiimidazoleHCID 102205613-(3-(Piperidin-1-ylmethyl)phenoxy)propan-1-amineHCID 19762511HCID 19762511, compound

Product 1

HCID 19762493N-[3-[N-[3-phenyl-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 0.74 g (2.6 mmol) of N-methyl-N-[3-phenyl-3-(2-pyridyl)propyl]-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.[%])=558 ([M+H]+, 11), 196 (100); IR (KBr): 1639 cm-1 (C=O). For analytical purposes a sample is converted into the maleic acid salt and recrystallised from ether/ethanol; m.p.: from 70° C. with decomposition.

Workup

  1. customPreparation
  2. custompurified title compound in the form of an oil
  3. customrecrystallised from ether/ethanol
  4. customfrom 70° C.

Sources & evidence

ORD record
ord-963dd2edfa274798bdff410eb4e62f1b
Source dataset
uspto-grants-1993_05
Patent number
US05212187

Reaction notes

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