N-[2-[N-(4-methoxybenzyl)-N-(2-pyridyl)amino]ethyl]-N-methyl-1,2-ethanediamine → N-[2-[N-[2-[N-(4-methoxybenzyl)-N-(2-pyridyl)amino]ethyl]-N-methylamino]ethyl]-N'-[3-[3-(piperidinomethyl)phenoxy]propyl]-2-nitro-1,1-ethenediamine

HRID 248997Notes

Reaction equation

HRID 248997 reaction equation
[CH3:1][O:2][C:3]1[CH:23]=[CH:22][C:6]([CH2:7][N:8]([CH2:15][CH2:16][N:17]([CH3:21])[CH2:18][CH2:19][NH2:20])[C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][N:10]=2)=[CH:5][CH:4]=1.CS[C:26]([NH:31][CH2:32][CH2:33][CH2:34][O:35][C:36]1[CH:41]=[CH:40][CH:39]=[C:38]([CH2:42][N:43]2[CH2:48][CH2:47][CH2:46][CH2:45][CH2:44]2)[CH:37]=1)=[CH:27][N+:28]([O-:30])=[O:29]>>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([CH2:7][N:8]([CH2:15][CH2:16][N:17]([CH2:18][CH2:19][NH:20][C:26]([NH:31][CH2:32][CH2:33][CH2:34][O:35][C:36]2[CH:41]=[CH:40][CH:39]=[C:38]([CH2:42][N:43]3[CH2:48][CH2:47][CH2:46][CH2:45][CH2:44]3)[CH:37]=2)=[CH:27][N+:28]([O-:30])=[O:29])[CH3:21])[C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][N:10]=2)=[CH:22][CH:23]=1

Participants

3

Reactant 2

HCID 19762590N-[2-[N-(4-methoxybenzyl)-N-(2-pyridyl)amino]ethyl]-N-methyl-1,2-ethanediamineHCID 678820931-Methylthio-1-[3-[3-(piperidinomethyl)phenoxy]propyl]amino-2-nitroethene

Product 1

HCID 67882061N-[2-[N-[2-[N-(4-methoxybenzyl)-N-(2-pyridyl)amino]ethyl]-N-methylamino]ethyl]-N'-[3-[3-(piperidinomethyl)phenoxy]propyl]-2-nitro-1,1-ethenediamine

Procedure

Preparation is effected analogously to Example 22, using 0.85 g (2.7 mmol) of N-[2-[N-(4-methoxybenzyl)-N-(2-pyridyl)amino]ethyl]-N-methyl-1,2-ethanediamine and the equimolar amount of 1-methylthio-1-[3-[3-(piperidinomethyl)phenoxy]propyl]amino-2-nitroethene as starting materials. Chromatographic working-up analogously to Example 22 yields the purified title compound in the form of a viscous oil; MS (+FAB method): m/z (rel. int. [%])=632 ([M+H]+, 8), 121 (100). For further analysis, a portion of the compound is converted into the tartaric acid salt and recrystallised from isopropanol/ether; m.p.: 102°-104° C. (isopropanol/ether).

Workup

  1. customPreparation
  2. customyields the
  3. custompurified title compound in the form of a viscous oil
  4. customrecrystallised from isopropanol/ether

Sources & evidence

ORD record
ord-435298b4a8a14f46b0d3a7bc89d77a7c
Source dataset
uspto-grants-1993_05
Patent number
US05212187

Reaction notes

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