2-(2-Aminoethyl)-5-methoxyindole → 6-Hydroxytryptamine

HRID 6738

Reaction equation

HRID 6738 reaction equation
[H-].C([Al+]CC(C)C)C(C)C.C[O:12][C:13]1[CH:21]=[C:20]2[C:16]([C:17]([CH2:22][CH2:23][NH2:24])=[CH:18][NH:19]2)=[CH:15][CH:14]=1>C1(C)C=CC=CC=1>[NH2:24][CH2:23][CH2:22][C:17]1[C:16]2[C:20](=[CH:21][C:13]([OH:12])=[CH:14][CH:15]=2)[NH:19][CH:18]=1

Participants

4

Reactant 2

HCID 176542-(2-Aminoethyl)-5-methoxyindoleHCID 21225700Diisobutylaluminumhydride

Product 1

HCID 1604636-HydroxytryptamineYield 68.2%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
0 °C

Procedure

Diisobutylaluminum hydride (1 M in toluene, 15 mL) was slowly added to a suspension of 2-(6-methoxy-1H-indol-3-yl)ethylamine (250 mg) in 20 mL of toluene. The resulting clear solution was refluxed for 10 h, then cooled to 0° C. and quenched by the careful addition of 20 mL of 1:1 methyl alcohol:water. The mixture was stirred for 15 min at rt and filtered to remove the precipitated aluminum salts. The solvent was evaporated to yield 158 mg of 3-(2-amino-ethyl)-1H-indol-6-ol.

Workup

  1. temperatureThe resulting clear solution was refluxed for 10 h
  2. customquenched by the careful addition of 20 mL of 1:1 methyl alcohol
  3. filtrationfiltered
  4. customto remove the precipitated aluminum salts
  5. customThe solvent was evaporated

Sources & evidence

ORD record
ord-e5c557f7a27d4624a1960146dfa584ae
Source dataset
uspto-grants-2006_08
Patent number
US07084154B2

Linked notes

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