Water → [3-(6,6-dimethyl-4,5,6,7-tetrahydro-1H-indol-3-yl)-propyl]-diethylamine

HRID 1372397Notes

Reaction equation

HRID 1372397 reaction equation
[CH3:1][C:2]1([CH3:21])[CH2:10][C:9]2[NH:8][CH:7]=[C:6]([CH2:11][CH2:12][C:13]([N:15]([CH2:18][CH3:19])[CH2:16][CH3:17])=O)[C:5]=2[C:4](=O)[CH2:3]1.[H-].[Al+3].[Li+].[H-].[H-].[H-].[OH-].[Na+].O>O1CCCC1>[CH3:21][C:2]1([CH3:1])[CH2:10][C:9]2[NH:8][CH:7]=[C:6]([CH2:11][CH2:12][CH2:13][N:15]([CH2:18][CH3:19])[CH2:16][CH3:17])[C:5]=2[CH2:4][CH2:3]1

Participants

6

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 225710523-(6,6-dimethyl-4-oxo-4,5,6,7-tetrahydro-1H-indol-3-yl)-N,N-diethylpropionamide

Product 1

HCID 22571045[3-(6,6-dimethyl-4,5,6,7-tetrahydro-1H-indol-3-yl)-propyl]-diethylamineYield 90.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a suspension of 3-(6,6-dimethyl-4-oxo-4,5,6,7-tetrahydro-1H-indol-3-yl)-N,N-diethyl-propionamide (1.1 g, 3.8 mmol) in tetrahydrofuran (80 mL) was added dropwise a solution of lithium aluminum hydride (0.57 g, 15.1 mmol) in tetrahydrofuran. The mixture was refluxed overnight. To the cooled reaction was added enough ice 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 0.9 g of [3-(6,6-dimethyl-4,5,6,7-tetrahydro-1H-indol-3-yl)-propyl]-diethyl-amine as a light yellow oil. 1H-NMR (360 MHz, dimethylsulfoxide-d6) δ 9.75 (br s, 1H, NH), 6.24 (s, 1H), 2.19–2.44 (m, 14H, 7×CH2), 1.53 (m, 2H, CH2), 1.40 (m, 2H, CH2), 0.88–0.92 (m, 12H, 4×CH3). MS m/z 262 [M+].

Workup

  1. temperatureThe mixture was refluxed overnight
  2. customTo the cooled reaction
  3. additionwas added enough ice until no more gas
  4. customthe insolubles removed by vacuum filtration
  5. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-f328655499934cb394171fc263c6d501
Source dataset
uspto-grants-2007_01
Patent number
US07157577B2

Reaction notes

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