Water → 3-[3-(4-methylpiperazin-1-yl)propyl]-4,5,6,7-tetrahydro-1H-indole

HRID 24339Notes

Reaction equation

HRID 24339 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[CH3:7][N:8]1[CH2:13][CH2:12][N:11]([C:14](=O)[CH2:15][CH2:16][C:17]2[C:25]3[C:24](=O)[CH2:23][CH2:22][CH2:21][C:20]=3[NH:19][CH:18]=2)[CH2:10][CH2:9]1.O>C1COCC1.[OH-].[Na+]>[CH3:7][N:8]1[CH2:9][CH2:10][N:11]([CH2:14][CH2:15][CH2:16][C:17]2[C:25]3[CH2:24][CH2:23][CH2:22][CH2:21][C:20]=3[NH:19][CH:18]=2)[CH2:12][CH2:13]1

Participants

6

Reactant 3

HCID 962WaterHCID 21226445Aluminium lithium hydrideHCID 225710693-[3-(4-Methylpiperazin-1-yl)-3-oxo-propyl]-1,5,6,7-tetrahydroindol-4-one

Product 1

HCID 225711153-[3-(4-methylpiperazin-1-yl)propyl]-4,5,6,7-tetrahydro-1H-indoleYield 101.3%

Reagents, catalysts & solvents 2

HCID 14798Sodium HydroxideCatalystHCID 8028TetrahydrofuranSolvent

Procedure

LAH (2.6 g, 68 mmol) was added dropwise to a suspension of 3-[3-(4-methylpiperazin-1-yl)-3-oxo-propyl]-1,5,6,7-tetrahydroindol-4-one (5 g, 17 mmol) in THF (300 mL). The mixture was then refluxed overnight. The mixture was then cooled and 2.6 mL each of water followed by a few drops of 15% NaOH was added. The reaction was stirred at room temperature for 30 min and then filtered to remove insolubles. The filtrate was concentrated to give 4.5 g (100%) of 3-[3-(4-methylpiperazin-1-yl)propyl]-4,5,6,7-tetrahydro-1H-indole.

Workup

  1. temperatureThe mixture was then refluxed overnight
  2. temperatureThe mixture was then cooled
  3. additionwas added
  4. filtrationfiltered
  5. customto remove insolubles
  6. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-8aef07f7b52743baa5ff07de3736c246
Source dataset
uspto-grants-2005_02
Patent number
US06855730B2

Reaction notes

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