Methanol → 5-(Aminomethyl)-1H-indole-3-propanol

HRID 441081Notes

Reaction equation

HRID 441081 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][CH:7]=[C:6]2[CH2:12][CH2:13][CH2:14][OH:15])#[N:2].CO.CC#N>C(O)C.[Pd]>[NH4+:2].[OH-:15].[NH2:2][CH2:1][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][CH:7]=[C:6]2[CH2:12][CH2:13][CH2:14][OH:15]

Participants

7

Reactant 3

HCID 887Methanol2×HCID 6342AcetonitrileHCID 224057113-(3-Hydroxypropyl)-1H-indole-5-carbonitrile

Product 2

HCID 14923Ammonium HydroxideHCID 224056935-(Aminomethyl)-1H-indole-3-propanolYield 131.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a solution of 5-cyano-3-(3-hydroxypropyl)indole (1.00 g, 0.005 mol) in 30 mL of absolute ethanol was added 10% palladium-on-charcoal (1.00 g) and the mixture was hydrogenated on a Parr shaker at 40 psi for 6 h. The mixture was then filtered, through Celite, the filtercake was washed with additional ethanol and the filtrate was evaporated to give a colourless gum. Flash chromatography (SiO2 /MeCN--MeOH, 9:1 then MeCN--MeOH--NH4OH, 90:9:1) afforded the essentially pure title compound (0.67 g, 70%) as a colourless gum: IR (neat) 3250 cm-1 ; 1H NMR (DMSO-d6, 200 MHz) δ 10.60 (s, 1H), 7.41 (s, 1H), 7.23 (d, J=8.2 Hz, 1H), 7.04 (s, 1H), 7.02 (d, J=8.1 Hz, 1H), 4.4 (br s, 1H), 3.75 (s, 2H), 3.46 (t, J=6.5 Hz, 2H), 3.3 (br s, 2H), 2.68 (m, 2H), 1.78 (m, 2H).

Workup

  1. filtrationThe mixture was then filtered, through Celite
  2. washthe filtercake was washed with additional ethanol
  3. customthe filtrate was evaporated
  4. customto give a colourless gum

Sources & evidence

ORD record
ord-2a496e94b60f41c2a445ee8ebc4f89ac
Source dataset
uspto-grants-1996_05
Patent number
US05521188

Reaction notes

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