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

HRID 1372411Notes

Reaction equation

HRID 1372411 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([C:8](=O)[CH2:9][CH2:10][C:11]2[C:19]3[C:18](=O)[CH2:17][CH2:16][CH2:15][C:14]=3[NH:13][CH:12]=2)[CH2:4][CH2:3]1.[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[OH-].[Na+]>O1CCCC1>[CH3:1][N:2]1[CH2:3][CH2:4][N:5]([CH2:8][CH2:9][CH2:10][C:11]2[C:19]3[CH2:18][CH2:17][CH2:16][CH2:15][C:14]=3[NH:13][CH:12]=2)[CH2:6][CH2:7]1

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 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 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a suspension of 3-[3-(4-methyl-piperazin-1-yl)-3-oxo-propyl]-1,5,6,7-tetrahydro-indol-4-one (5 g, 17 mmol) in 300 mL of tetrahydrofuran was added dropwise a solution of lithium aluminum hydride in tetrahydrofuran (2.6 g, 68 mmol). The mixture was heated to reflux overnight. To the cooled reaction was sequentially added 2.6 mL each of water, 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 4.5 g (100% yield) of 3-[3-(4-methyl-piperazin-1-yl)-propyl]-4,5,6,7-tetrahydro-1H-indole. 1H-NMR (360 MHz, dimethylsulfoxide-d6) δ 9.79 (br s, 1H, NH), 6.22 (d, 1H), 2.44 (m, 2H, CH2), 2.21–2.30 (m, 14H, 7×CH2), 2.12 (s, 3H, CH3), 1.65 (m, 4H, 2×CH2), 1.53 (m, 2H, CH2). MS m/z 261 [M+].

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux overnight
  3. customTo the cooled reaction
  4. customthe insolubles removed by vacuum filtration
  5. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-159ca87c693d49c68bb1c8f923f7fabf
Source dataset
uspto-grants-2007_01
Patent number
US07157577B2

Reaction notes

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