Nitrogen → 3-[(beta-Benzylamino)ethyl]indole

HRID 1094598Notes

Reaction equation

HRID 1094598 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([C:10](=[CH:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:11]#[N:12])=[CH:2]1.N#N>CCO>[CH2:13]([CH:10]([C:3]1[C:4]2[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=2)[NH:1][CH:2]=1)[CH2:11][NH2:12])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

4

Reactant 2

HCID 947NitrogenHCID 666408512-1H-indol-3-yl-3-phenylacrylonitrile

Product 1

HCID 5829313-[(beta-Benzylamino)ethyl]indole

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

β-Benzyltryptamine was prepared by the addition of 2-1H-indol-3-yl-3-phenylacrylonitrile (500 mg, 2.04 mmol) and EtOH (25 mL) to a N2 purged 100 mL flask. To the solution was added approximately 2 g of Raney-Ni slurry. To the reaction solution, dropwise with stirring, was added hydrazine monohydrate (2.5 mL). The reaction solution was allowed to stir at 65° C. for 4 hours. The slurry was filtered through a pad of Celite to remove excess Raney-Ni. The filtrate was concentrated under reduced pressure, and the crude product was used without further purification; MS (ESI): 251 (MH+).

Workup

  1. custompurged 100 mL flask
  2. additionTo the solution was added approximately 2 g of Raney-Ni slurry
  3. additionwas added hydrazine monohydrate (2.5 mL)
  4. stirringto stir at 65° C. for 4 hours
  5. filtrationThe slurry was filtered through a pad of Celite
  6. customto remove excess Raney-Ni
  7. concentrationThe filtrate was concentrated under reduced pressure
  8. customthe crude product was used without further purification

Sources & evidence

ORD record
ord-84f6efad7b0347e496196bf71c3c6090
Source dataset
uspto-grants-2012_03
Patent number
US08133992B2

Reaction notes

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