Water → N-(6-methoxyindan-1-ylmethyl)amine
Reaction equation
[CH3:1][O:2][C:3]1[CH:11]=[C:10]2[C:6]([CH2:7][CH2:8][CH:9]2[CH2:12][N:13]=[N+]=[N-])=[CH:5][CH:4]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[OH-].[Na+]>C(OCC)C>[CH3:1][O:2][C:3]1[CH:11]=[C:10]2[C:6]([CH2:7][CH2:8][CH:9]2[CH2:12][NH2:13])=[CH:5][CH:4]=1Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
20 g (0.1 mol) of 6-methoxyindan-1-ylmethylazide are dissolved in 400 ml of diethyl ether and added dropwise, at 25°-30°, to a suspension of 5.0 g (0.13 mol) of lithium aluminium hydride in 200 ml of diethyl ether. When the addition has been completed, the mixture is maintained under reflux for 6 hours and, while cooling with ice, 5 ml of water, 5 ml of 15% sodium hydroxide solution and 15 ml of water are added thereto. The white precipitate which has formed is filtered off and boiled up 3 times with dichloromethane. The organic filtrates are combined, dried over magnesium sulphate and concentrated to dryness by evaporation in vacuo. The N-(6-methoxyindan-1-ylmethyl)amine which is obtained as an oily residue is converted into the hydrochloride with ethereal hydrochloric acid and recrystallised from isopropanol/diethyl ether. The pure 6-methoxyindan-1ylmethylammonium chloride melts at 129°-131°.
Workup
- additionWhen the addition
- temperaturethe mixture is maintained
- temperatureunder reflux for 6 hours
- additionare added
- customThe white precipitate which has formed
- filtrationis filtered off
- dry with materialdried over magnesium sulphate
- concentrationconcentrated to dryness by evaporation in vacuo
Sources & evidence
- ORD record
- ord-8e87113a2fd7448893bbaf75cb502da0
- Source dataset
- uspto-grants-1990_07
- Patent number
- US04939160
Reaction notes
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