Aluminium lithium hydride → 3-(3-piperazin-1-ylpropyl)-4,5,6,7-tetrahydro-1H-indole

HRID 1836134Notes

Reaction equation

HRID 1836134 reaction equation
O=[C:2]([N:15]1[CH2:20][CH2:19][NH:18][CH2:17][CH2:16]1)[CH2:3][CH2:4][C:5]1[C:13]2[C:12](=O)[CH2:11][CH2:10][CH2:9][C:8]=2[NH:7][CH:6]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].ClCCl.CO.N>O1CCOCC1.O1CCCC1>[N:15]1([CH2:2][CH2:3][CH2:4][C:5]2[C:13]3[CH2:12][CH2:11][CH2:10][CH2:9][C:8]=3[NH:7][CH:6]=2)[CH2:20][CH2:19][NH:18][CH2:17][CH2:16]1

Participants

6

Reactant 3

HCID 21226445Aluminium lithium hydrideHCID 21584172Ammonia methanol dichloromethaneHCID 23498812HCID 23498812, compound

Product 1

HCID 234988493-(3-piperazin-1-ylpropyl)-4,5,6,7-tetrahydro-1H-indoleYield 79%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
70 °C

Procedure

3-(3-Oxo-3-piperazin-1-yl-propyl)-1,5,6,7-tetrahydro-indol-4-one (3.8 g, 75% pure) was dissolved in 1,4-dioxane (4×50 ml) and was added to a mixture of lithium aluminum hydride (3.9 g, 7 equiv.) in 50 ml of tetrahydrofuran at 0° C. The reaction mixture was refluxed at 70° C. overnight. Thin layer chromatography (dichloromethane: methanol: ammonia 5:1:0.1) showed one major spot. The reaction mixture was quenched by DI water (6 ml), 10% sodium hydroxide (14 ml) and DI water (15 ml). The formed solid was filtered out and washed twice with 1,4-dioxane. The filtrate was concentrated and dried under high vacuum to give 3-(3-piperazin-1-yl-propyl)-4,5,6,7-tetrahydro-1H-indole (2.3 g, 79% pure).

Workup

  1. customThe reaction mixture was quenched by DI water (6 ml), 10% sodium hydroxide (14 ml) and DI water (15 ml)
  2. filtrationThe formed solid was filtered out
  3. washwashed twice with 1,4-dioxane
  4. concentrationThe filtrate was concentrated
  5. customdried under high vacuum

Sources & evidence

ORD record
ord-01fd1a84cd894f4eae36881fc325c65f
Source dataset
uspto-grants-2004_08
Patent number
US06777417B2

Reaction notes

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