N-[3-(4-chlorophenyl)-3-(2-pyridyl)propyl]-N-methyl-1,7-heptanediamine → Ammonia
Reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][N:22]=2)[CH2:9][CH2:10][N:11]([CH3:20])[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][NH2:19])=[CH:4][CH:3]=1.CS[C:29]([NH:34][CH2:35][CH2:36][CH2:37][O:38][C:39]1[CH:44]=[CH:43][CH:42]=[C:41]([CH2:45][N:46]2[CH2:51][CH2:50][CH2:49][CH2:48][CH2:47]2)[CH:40]=1)=[CH:30][N+:31]([O-:33])=[O:32].C(OCC)(=O)C.CO>C(#N)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][N:22]=2)[CH2:9][CH2:10][N:11]([CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][NH:19][C:29]([NH:34][CH2:35][CH2:36][CH2:37][O:38][C:39]2[CH:44]=[CH:43][CH:42]=[C:41]([CH2:45][N:46]3[CH2:51][CH2:50][CH2:49][CH2:48][CH2:47]3)[CH:40]=2)=[CH:30][N+:31]([O-:33])=[O:32])[CH3:20])=[CH:4][CH:3]=1.[NH3:11]Participants
6
Reactant 3
Product 2
Reagents, catalysts & solvents 1
Procedure
A mixture of 0.73 g (1.9 mmol) of N-[3-(4-chlorophenyl)-3-(2-pyridyl)propyl]-N-methyl-1,7-heptanediamine 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 of 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, ammonia atmosphere); MS (+FAB method): m/z (rel. int. [%])=691 ([M+H]30 12), 230 (100).
Sources & evidence
- ORD record
- ord-4626132b314748ffb6e6454d5c025e81
- Source dataset
- uspto-grants-1993_05
- Patent number
- US05212187
Reaction notes
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