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

HRID 911335Notes

Reaction equation

HRID 911335 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-27417993bdfe41579a0c31df9f46ca43
Source dataset
uspto-grants-2011_09
Patent number
US08022062B2

Reaction notes

Loading…