2-(1H-indol-3-yl)propanenitrile → beta-Methyltryptamine
Reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[NH:7]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[C:9]([CH:16]([CH3:19])[C:17]#[N:18])=[CH:8]1>C1COCC1>[NH:7]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[C:9]([CH:16]([CH3:19])[CH2:17][NH2:18])=[CH:8]1Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
To a stirred suspension of LAH (3.4 g, 90 mmol) in THF (40 mL, anhyd) chilled to 0° C. was added a solution of 2-(1H-indol-3-yl)propionitrile (2.5 g, 14.7 mmol) in THF (40 mL, anhyd). The reaction mixture was allowed to warm to ambient temperature and then heated at reflux. After 1 hour, the reaction mixture was cooled to 0° C. and quenched cautiously with wet THF (5-10% H2O) until gas evolution had ceased. The resulting mixture was filtered through Celite™ and concentrated to give a brown residue. The filtering agent was rinsed with Et2O (100 mL), which was combined with the residue, dried (Na2SO4), and concentrated under reduced pressure to yield 2-(1H-indol-3-yl)propylamine (2.1 g, 82%) as a pale amber oil; 1H-NMR (CDCl3): δ 8.28 (1H, br s), 7.61 (1H, d), 7.36 (1H, d), 7.16 (1H, app t), 7.08 (1H, app t), 6.96 (1H, br s), 3.41 (2H, br s), 3.19 (1H, q), 2.95 (2H, app d), 1.35 (3H, d).
Workup
- temperatureto warm to ambient temperature
- temperatureheated
- temperatureat reflux
- temperaturethe reaction mixture was cooled to 0° C.
- customquenched cautiously with wet THF (5-10% H2O) until gas evolution
- filtrationThe resulting mixture was filtered through Celite™
- concentrationconcentrated
- customto give a brown residue
- washThe filtering agent was rinsed with Et2O (100 mL), which
- dry with materialdried (Na2SO4)
- concentrationconcentrated under reduced pressure
Sources & evidence
- ORD record
- ord-a01ab38fe4e542948c0c9c503bf46590
- Source dataset
- uspto-grants-2013_09
- Patent number
- US08524704B2
Reaction notes
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