5-Benzyl-3-(2-nitroethenyl)indole → 3-(2-Aminoethyl)-5-benzylindole

HRID 1720067Notes

Reaction equation

HRID 1720067 reaction equation
[CH2:1]([C:8]1[CH:9]=[C:10]2[C:14](=[CH:15][CH:16]=1)[NH:13][CH:12]=[C:11]2[CH:17]=[CH:18][N+:19]([O-])=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>C1COCC1>[NH2:19][CH2:18][CH2:17][C:11]1[C:10]2[C:14](=[CH:15][CH:16]=[C:8]([CH2:1][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)[CH:9]=2)[NH:13][CH:12]=1

Participants

3

Reactant 1

HCID 544807005-Benzyl-3-(2-nitroethenyl)indole

Product 1

HCID 153425493-(2-Aminoethyl)-5-benzylindoleYield 45%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of the 5-benzyl-3-(2-nitroethenyl)indole (0.1 g, 0.4 mmol)in dry THF was added dropwise to a cooled (ice bath) suspension of LiAIH4 (0.1 g, 2.4 mmol)in 5 ml of dry THF under nitrogen. The mixture was heated at reflux for 45 min. Excess LiAIH4 was destroyed by successive addition of H2O (0.15 ml), 15% NaOH (0.15 ml) and H2O (0.4 ml). The white precipitate was removed by filtration and washed with THF (10 ml). After drying (MgSO4), the flitrate was evaporated under reduced pressure to give 0.04 g (45%) of 3-(2-aminoethyl)-5-benzylindole as a free base. The free base was converted to the fumarate salt, mp 150°-153° C.

Workup

  1. temperaturea cooled
  2. temperatureThe mixture was heated
  3. temperatureat reflux for 45 min
  4. customExcess LiAIH4 was destroyed by successive addition of H2O (0.15 ml), 15% NaOH (0.15 ml) and H2O (0.4 ml)
  5. customThe white precipitate was removed by filtration
  6. washwashed with THF (10 ml)
  7. dry with materialAfter drying (MgSO4)
  8. customthe flitrate was evaporated under reduced pressure

Sources & evidence

ORD record
ord-30ecb9bb1044471fb707a1ebee44c240
Source dataset
uspto-grants-1996_04
Patent number
US05504101

Reaction notes

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