Ethanol → 2-(1-(2-cyclohexylethyl)-5-methyl-1H-indol-3-yl)-N-methylethanamine
Reaction equation
[CH:1]1([CH2:7][CH2:8][N:9]([C:11]2[CH:16]=[CH:15][C:14]([CH3:17])=[CH:13][CH:12]=2)N)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.CCO.C(O[CH:24](OCC)[CH2:25][CH2:26][CH2:27][NH:28][CH3:29])C>O.Cl>[CH:1]1([CH2:7][CH2:8][N:9]2[C:11]3[C:16](=[CH:15][C:14]([CH3:17])=[CH:13][CH:12]=3)[C:25]([CH2:26][CH2:27][NH:28][CH3:29])=[CH:24]2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1Participants
6
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 90 °C
Procedure
The title compound was prepared by General Method 3. A solution of 1-(2-cyclohexylethyl)-1-p-tolylhydrazine (0.15 g) in water (1 mL) and conc. HCl (0.18 mL) was heated to 60° C. EtOH (1 mL) was added followed by 4,4-diethoxy-N-methylbutan-1-amine (0.12 g) and the temperature was raised to 90° C. Conc. HCl (0.1 mL) was added and the heating was continued for an additional 6 h after which the reaction mixture was cooled and stirred at 25° C. for 12 h. The reaction mixture was concentrated under reduced pressure and the residue was purified by silica gel chromatography (eluent EtOAc/EtOH/NH3: 9/1/0.1) to obtain 79 mg of product.
Workup
- temperatureafter which the reaction mixture was cooled
- concentrationThe reaction mixture was concentrated under reduced pressure
- customthe residue was purified by silica gel chromatography (eluent EtOAc/EtOH/NH3: 9/1/0.1)
Sources & evidence
- ORD record
- ord-70c58b44710f4c489f20e4dc7bc181bf
- Source dataset
- uspto-grants-2012_12
- Patent number
- US08338447B2
Reaction notes
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