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

HRID 248956Notes

Reaction equation

HRID 248956 reaction equation
[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: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>[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: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])[CH3:15])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 682631,1'-CarbonyldiimidazoleHCID 102205613-(3-(Piperidin-1-ylmethyl)phenoxy)propan-1-amineHCID 19762518N-[3-(4-chlorophenyl)-3-(2-pyridyl)propyl]-N-methyl-1,2-ethanediamine

Product 1

HCID 19762585N-[2-[N-[3-(4-chlorophenyl)-3-(2-pyridyl)propyl]-N-methylamino]ethyl]-N'-[3-[3-(piperidinomethyl)phenoxy]propyl]urea

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Preparation is effected analogously to Example 63, using 0.92 g (3 mmol) of N-[3-(4-chlorophenyl)-3-(2-pyridyl)propyl]-N-methyl-1,2-ethanediamine, an equimolar amount of 1,1'-carbonyldiimidazole and 0.88 g (3.5 mmol) of 3-[3-(piperidinomethyl)phenoxy]propaneamine as starting materials. Working up by chromatography (eluant: ethyl acetate) analogously to Example 63 yields the purified title compound in the form of an oil; MS (+FAB method): m/z (rel. int.[%])=578 ([M+H]+, 2), 230 (38), 78 (100); IR (KBr): 1637 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.: 99°-105° C.

Workup

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

Sources & evidence

ORD record
ord-360a4364dfb745599990e638bb4e46c8
Source dataset
uspto-grants-1993_05
Patent number
US05212187

Reaction notes

Loading…