Potassium Iodide → 1-Acetyl-5-[2-[2-(2-ethoxyphenoxy)ethylamino]propyl]indoline-7-carbonitrile
Reaction equation
[C:1]([N:4]1[C:12]2[C:7](=[CH:8][C:9]([CH2:15][CH:16](Br)[CH3:17])=[CH:10][C:11]=2[C:13]#[N:14])[CH2:6][CH2:5]1)(=[O:3])[CH3:2].[CH2:19]([O:21][C:22]1[CH:31]=[CH:30][CH:29]=[CH:28][C:23]=1[O:24][CH2:25][CH2:26][NH2:27])[CH3:20].[I-].[K+].C1OCCOCCOCCOCCOCCOC1>O1CCOCC1>[C:1]([N:4]1[C:12]2[C:7](=[CH:8][C:9]([CH2:15][CH:16]([NH:27][CH2:26][CH2:25][O:24][C:23]3[CH:28]=[CH:29][CH:30]=[CH:31][C:22]=3[O:21][CH2:19][CH3:20])[CH3:17])=[CH:10][C:11]=2[C:13]#[N:14])[CH2:6][CH2:5]1)(=[O:3])[CH3:2]Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of 1-acetyl-5-(2-bromopropyl)indoline-7-carbonitrile (300 mg) and 2-(2-ethoxyphenoxy)ethylamine (391 mg) in dioxane (4 ml) were added potassium iodide (17 mg) and 18-crown-6 (26 mg), and the mixture was reacted in a sealed tube at 180° C. for 18 hours. The reaction mixture was concentrated under reduced pressure, and the residue was purified by flash column chromatography on silica gel using a mixture of methylene chloride and methanol (40/1) as eluent to give 111 mg of 1-acetyl-5-[2-[2-(2-ethoxyphenoxy)ethylamino] propyl]indoline-7-carbonitrile as an oil.
Workup
- customthe mixture was reacted in a sealed tube at 180° C. for 18 hours
- concentrationThe reaction mixture was concentrated under reduced pressure
- customthe residue was purified by flash column chromatography on silica gel using
- additiona mixture of methylene chloride and methanol (40/1) as eluent
Sources & evidence
- ORD record
- ord-e53de1fde71a4a9685917c3b4ede803c
- Source dataset
- uspto-grants-1995_02
- Patent number
- US05387603
Reaction notes
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