3-(2-dimethylamino-ethyl)-1H-indole-5-carbaldehyde → 5-Hydroxymethyl-N,N-dimethyltryptamine

HRID 71040Notes

Reaction equation

HRID 71040 reaction equation
[CH3:1][N:2]([CH3:16])[CH2:3][CH2:4][C:5]1[C:13]2[C:8](=[CH:9][CH:10]=[C:11]([CH:14]=[O:15])[CH:12]=2)[NH:7][CH:6]=1>CO>[CH3:16][N:2]([CH3:1])[CH2:3][CH2:4][C:5]1[C:13]2[C:8](=[CH:9][CH:10]=[C:11]([CH2:14][OH:15])[CH:12]=2)[NH:7][CH:6]=1

Participants

3

Reactant 1

HCID 99908943-(2-dimethylamino-ethyl)-1H-indole-5-carbaldehyde

Product 1

HCID 102628495-Hydroxymethyl-N,N-dimethyltryptamineYield 104.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A 50 ml hydrogenation bomb is charged with 3-(2-dimethylamino-ethyl)-1H-indole-5-carbaldehyde (Example 13) (1.0 g, 4.62 mmol) and methanol (10 mL). The bomb is purged with hydrogen (three times to 200 psi and release to atmospheric pressure), and then pressurised to 200 psi. After stirring for one hour, the pressure is released, and a solution of [Rh DiPFc (COD)]BF4 (6.6 mg, S/C=500) in methanol (1 ml) is added through a septum port. The bomb is pressurized with hydrogen to 200 psi, and left stirring at ambient temperature for 18 hours. Removal of the solvent from the hydrogenation mixture gives the title product (1.05 g, quant.) as an oil.

Workup

  1. customThe bomb is purged with hydrogen (three times to 200 psi and release to atmospheric pressure)
  2. additiona solution of [Rh DiPFc (COD)]BF4 (6.6 mg, S/C=500) in methanol (1 ml) is added through a septum port
  3. waitleft
  4. stirringstirring at ambient temperature for 18 hours
  5. customRemoval of the solvent from the hydrogenation mixture

Sources & evidence

ORD record
ord-6ab4bc50872d4219b231a2c439a54d94
Source dataset
uspto-grants-2014_09
Patent number
US08822702B2

Reaction notes

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