Water → [3-(6,6-dimethyl-4,5,6,7-tetrahydro-1H-indol-3-yl)-propyl]-dimethyl-amine
Reaction equation
[CH3:1][C:2]1([CH3:19])[CH2:10][C:9]2[NH:8][CH:7]=[C:6]([CH2:11][CH2:12][C:13]([N:15]([CH3:17])[CH3:16])=O)[C:5]=2[C:4](=O)[CH2:3]1.[H-].[Al+3].[Li+].[H-].[H-].[H-].[OH-].[Na+].O>O1CCCC1>[CH3:1][C:2]1([CH3:19])[CH2:10][C:9]2[NH:8][CH:7]=[C:6]([CH2:11][CH2:12][CH2:13][N:15]([CH3:17])[CH3:16])[C:5]=2[CH2:4][CH2:3]1Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
To a suspension of 3-(6,6-dimethyl-4-oxo-4,5,6,7-tetrahydro-1H-indol-3-yl)-N,N-dimethyl-propionamide (1.2 g, 4.68 mmol) in tetrahydrofuran (30 mL) was added dropwise a solution of lithium aluminum hydride (0.69 g, 18.3 mmol) in tetrahydrofuran. The mixture was refluxed overnight. Ice was added to the cooled reaction until no more gas was generated followed by 15% sodium hydroxide and water. The reaction was stirred at room temperature for 30 minutes and the insolubles removed by vacuum filtration. The filtrate was concentrated to give [3-(6,6-dimethyl-4,5,6,7-tetrahydro-1H-indol-3-yl)-propyl]-dimethyl-amine as an oil. 1H-NMR (360 MHz, dimethylsulfoxide-d6) δ 9.75 (br s, 1H, NH), 6.24 (s, 1H), 3.36 (m, 2H, CH2), 2.07–2.3 (m, 14H, 7×CH2), 1.53 (m, 2H, CH2), 1.40 (m, 2H, CH2), 0.92 (s, 6H, 2×CH3). MS m/z 234 [M+].
Workup
- temperatureThe mixture was refluxed overnight
- additionIce was added to the cooled reaction until no more gas
- customthe insolubles removed by vacuum filtration
- concentrationThe filtrate was concentrated
Sources & evidence
- ORD record
- ord-073284754d444482a7c6e4eea5e743be
- Source dataset
- uspto-grants-2007_01
- Patent number
- US07157577B2
Reaction notes
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