Aluminium lithium hydride → 4-(Aminomethyl)-1-methyl-1H-indole

HRID 2041223Notes

Reaction equation

HRID 2041223 reaction equation
[CH3:1][N:2]1[C:10]2[CH:9]=[CH:8][CH:7]=[C:6]([C:11]#[N:12])[C:5]=2[CH:4]=[CH:3]1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>C1COCC1>[NH2:12][CH2:11][C:6]1[CH:7]=[CH:8][CH:9]=[C:10]2[C:5]=1[CH:4]=[CH:3][N:2]2[CH3:1]

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 223915921-Methyl-1H-indole-4-carbonitrile

Product 1

HCID 185257844-(Aminomethyl)-1-methyl-1H-indoleYield 91%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
50 °C

Procedure

Dissolve 1-methylindole-4-carbonitrile (1.0 g, 6.18 mmol) in anhydrous THF (10 mL) and add slowly to 1M lithium aluminum hydride in THF (12.4 mL, 12.37 mmol) at ambient temperature. Heat the reaction mixture at 50° C. for 17 h and cool to ambient temperature. Quench the reaction mixture with water until a granular precipitate starts to form and filter through a pad of Celite®. Evaporate the solvent and purify by SCX chromatography to obtain the title compound as a yellow oil (0.9 g, 91%). GC-MS m/z: 160 (M+).

Workup

  1. temperaturecool to ambient temperature
  2. customQuench the reaction mixture with water until a granular precipitate
  3. customto form
  4. filtrationfilter through a pad of Celite®
  5. customEvaporate the solvent
  6. custompurify by SCX chromatography

Sources & evidence

ORD record
ord-68fbf7d9abb34018b0b2eb0e19b0261b
Source dataset
uspto-grants-2013_11
Patent number
US08580780B2

Reaction notes

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