Aluminium lithium hydride → 3-[(4-methylpiperazin-1-yl)methyl]-1H-indole

HRID 254191Notes

Reaction equation

HRID 254191 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([C:10]([N:12]2[CH2:17][CH2:16][N:15]([CH3:18])[CH2:14][CH2:13]2)=O)=[CH:2]1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>C1COCC1>[CH3:18][N:15]1[CH2:16][CH2:17][N:12]([CH2:10][C:3]2[C:4]3[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=3)[NH:1][CH:2]=2)[CH2:13][CH2:14]1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 21854014HCID 21854014, compound

Product 1

HCID 2275843-[(4-methylpiperazin-1-yl)methyl]-1H-indole

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

(1H-Indol-3-yl)-(4-methylpiperazin-1-yl)methanone (2.44 g, 0.01 moles) in THF was treated with cooled and stirred suspension of Lithium aluminum hydride (g, 0.011 moles in THF slowly over the period of 2 to 5 hours, the reaction mixture was heated to reflux for 2-4 hours, after the completion of reaction, the reaction mixture was poured on to the ice and the compound was extracted in ethyl acetate. The residue obtained was purified by flash chromatography (silica gel, EtOAc/Hexanes, 2/8) to afford the compound, which was identified by IR, NMR and mass spectral analyses as the title compound.

Workup

  1. temperaturewith cooled
  2. temperaturethe reaction mixture was heated
  3. temperatureto reflux for 2-4 hours
  4. customafter the completion of reaction
  5. extractionthe compound was extracted in ethyl acetate
  6. customThe residue obtained
  7. customwas purified by flash chromatography (silica gel, EtOAc/Hexanes, 2/8)
  8. customto afford the compound, which

Sources & evidence

ORD record
ord-db9fb9c74c724df1a2c7e0c692015dc6
Source dataset
uspto-grants-2011_01
Patent number
US07875605B2

Reaction notes

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