N-[3-(4-fluorophenyl)-3-(2-pyridyl)propyl]-N-methyl-1,3-propanediamine → N-[3-[N-[3-(4-fluorophenyl)-3-(2-pyridyl)propyl]-N-methylamino]propyl]-N'-[3-[3-(piperidinomethyl)phenoxy]propyl]-2-nitro-1,1-ethenediamine

HRID 248952Notes

Reaction equation

HRID 248952 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.CS[C:25]([NH:30][CH2:31][CH2:32][CH2:33][O:34][C:35]1[CH:40]=[CH:39][CH:38]=[C:37]([CH2:41][N:42]2[CH2:47][CH2:46][CH2:45][CH2:44][CH2:43]2)[CH:36]=1)=[CH:26][N+:27]([O-:29])=[O:28].C(OCC)(=O)C.CO>C(#N)C>[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:25]([NH:30][CH2:31][CH2:32][CH2:33][O:34][C:35]2[CH:40]=[CH:39][CH:38]=[C:37]([CH2:41][N:42]3[CH2:47][CH2:46][CH2:45][CH2:44][CH2:43]3)[CH:36]=2)=[CH:26][N+:27]([O-:29])=[O:28])[CH3:16])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 19762608N-[3-(4-fluorophenyl)-3-(2-pyridyl)propyl]-N-methyl-1,3-propanediamineHCID 21584119Ethylacetate methanolHCID 678820931-Methylthio-1-[3-[3-(piperidinomethyl)phenoxy]propyl]amino-2-nitroethene

Product 1

HCID 67882031N-[3-[N-[3-(4-fluorophenyl)-3-(2-pyridyl)propyl]-N-methylamino]propyl]-N'-[3-[3-(piperidinomethyl)phenoxy]propyl]-2-nitro-1,1-ethenediamine

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 0.74 g (2.5 mmol) of N-[3-(4-fluorophenyl)-3-(2-pyridyl)propyl]-N-methyl-1,3-propanediamine and an equimolar amount of 1-methylthio-1-[3-[3-(piperidinomethyl)phenoxy]propyl]amino-2-nitro-ethene is heated under reflux for 12 hours in 20 ml of acetonitrile. The batch is then freed from solvent and the title compound is isolated in the form of a viscous oil by means of preparative thick-layer chromatography (eluant: ethyl acetate/methanol 9+1, ammoniacal atmosphere); MS (+FAB method): m/z (rel. int.[%])=619 ([M+H]+ 2), 214 (100). For analytical purposes a sample is converted into the O,O'-ditoluoyltartaric acid salt and recrystallised from ether/isopropanol; m.p.: from 102° C. with decomposition.

Sources & evidence

ORD record
ord-dcb1dec441fd4c708fd95a488c9cd1df
Source dataset
uspto-grants-1993_05
Patent number
US05212187

Reaction notes

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