2-(1H-indol-3-yl)propanenitrile → beta-Methyltryptamine

HRID 1258049Notes

Reaction equation

HRID 1258049 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[NH:7]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[C:9]([CH:16]([CH3:19])[C:17]#[N:18])=[CH:8]1>C1COCC1>[NH:7]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[C:9]([CH:16]([CH3:19])[CH2:17][NH2:18])=[CH:8]1

Participants

4

Reactant 2

HCID 122007942-(1H-indol-3-yl)propanenitrileHCID 21226445Aluminium lithium hydride

Product 1

HCID 6452095beta-MethyltryptamineYield 82%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

To a stirred suspension of LAH (3.4 g, 90 mmol) in THF (40 mL, anhyd) chilled to 0° C. was added a solution of 2-(1H-indol-3-yl)propionitrile (2.5 g, 14.7 mmol) in THF (40 mL, anhyd). The reaction mixture was allowed to warm to ambient temperature and then heated at reflux. After 1 h the reaction mixture was cooled to 0° C. and quenched cautiously with wet THF (5-10% H2O) until gas evolution had ceased. The resulting mixture was filtered through Celite™ and concentrated to give a brown residue. The filtering agent was rinsed with Et2O (100 mL), which was combined with the residue, dried (Na2SO4), and concentrated under reduced pressure to yield the title compound (2.1 g, 82%) as a pale amber oil. 1H-NMR (CDCl3): δ 8.28 (1 H, br s), 7.61 (1H, d), 7.36 (1H, d), 7.16 (1H, app t), 7.08 (1H, app t), 6.96 (1H, br s), 3.41 (2H, br s), 3.19 (1H, q), 2.95 (2H, app d), 1.35 (3H, d).

Workup

  1. temperatureto warm to ambient temperature
  2. temperatureheated
  3. temperatureat reflux
  4. temperatureAfter 1 h the reaction mixture was cooled to 0° C.
  5. customquenched cautiously with wet THF (5-10% H2O) until gas evolution
  6. filtrationThe resulting mixture was filtered through Celite™
  7. concentrationconcentrated
  8. customto give a brown residue
  9. washThe filtering agent was rinsed with Et2O (100 mL), which
  10. dry with materialdried (Na2SO4)
  11. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-961f608066c7482bb6f340fbf7c47319
Source dataset
uspto-grants-2013_06
Patent number
US08466143B2

Reaction notes

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