HCID 53750430, compound → HCID 22419950, compound

HRID 1720071Notes

Reaction equation

HRID 1720071 reaction equation
[CH2:1]([C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[NH:14][CH:13]=[C:12]2[CH:18]=[CH:19][N+:20]([O-])=O)[CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1>C1COCC1>[NH2:20][CH2:19][CH2:18][C:12]1[C:11]2[C:15](=[CH:16][CH:17]=[C:9]([CH2:1][CH2:2][C:3]3[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=3)[CH:10]=2)[NH:14][CH:13]=1

Participants

3

Reactant 1

HCID 53750430HCID 53750430, compound

Product 1

HCID 22419950HCID 22419950, compoundYield 56%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of the 5-phenethyl-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 precipitate was removed by filtration and washed with THF (10 ml). After drying (MgSO4), the filtrate was evaporated under reduced pressure to give (56% yield) 3-(2-aminoethyl)-5-(2-phenylethyl)indole, a beige solid; mp 234°-236° 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 precipitate was removed by filtration
  6. washwashed with THF (10 ml)
  7. dry with materialAfter drying (MgSO4)
  8. customthe filtrate was evaporated under reduced pressure

Sources & evidence

ORD record
ord-09e3f473474b484ab1d32b8c729d7d8d
Source dataset
uspto-grants-1996_04
Patent number
US05504101

Reaction notes

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