4-[3-(diethylamino)propoxy]Benzenamine → HCID 178418991, compound
Reaction equation
[CH2:1]([N:3]([CH2:15][CH3:16])[CH2:4][CH2:5][CH2:6][O:7][C:8]1[CH:13]=[CH:12][C:11]([NH2:14])=[CH:10][CH:9]=1)[CH3:2].[CH3:17][C:18]1[CH:26]=[CH:25][CH:24]=[C:23]2[C:19]=1[C:20](=[CH:28]O)[C:21](=[O:27])[NH:22]2>C1COCC1>[CH2:15]([N:3]([CH2:1][CH3:2])[CH2:4][CH2:5][CH2:6][O:7][C:8]1[CH:9]=[CH:10][C:11]([NH:14][CH:28]=[C:20]2[C:19]3[C:23](=[CH:24][CH:25]=[CH:26][C:18]=3[CH3:17])[NH:22][C:21]2=[O:27])=[CH:12][CH:13]=1)[CH3:16]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 72 °C
Procedure
To a solution of 4-(3-diethylamino-propoxy)-phenylamine (913 mg, 1.3 equiv.) in THF (14 mL) is added 4-methyl-3-hydroxymethylene-1,3-dihydro-indol-2-one (554 mg, 3.17 mmol) in one portion. The resulting reaction mixture is stirred and heated at 72° C. overnight. The reaction solution is cooled to room temperature and partitioned between EtOAc:H2O. The organic layer is collected and washed with saturated aqueous NaHCO3 and dried over anhydrous Na2SO4. The organic phase is filtered and concentrated. The residue obtained is triturated with 1:4 EtOAc:hexane to give the named compound as a yellow solid (625.8 mg, 52%).
Workup
- customThe resulting reaction mixture
- temperatureThe reaction solution is cooled to room temperature
- custompartitioned between EtOAc
- customThe organic layer is collected
- washwashed with saturated aqueous NaHCO3
- dry with materialdried over anhydrous Na2SO4
- filtrationThe organic phase is filtered
- concentrationconcentrated
- customThe residue obtained
- customis triturated with 1:4 EtOAc
Sources & evidence
- ORD record
- ord-88fce50e6ab94fb1bac2e93b1b221214
- Source dataset
- uspto-grants-2008_08
- Patent number
- US07414054B2
Reaction notes
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