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

HRID 2427916Notes

Reaction equation

HRID 2427916 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-ac5b2d70785c43c8a6a3e677abe3b28c
Source dataset
uspto-grants-2011_06
Patent number
US07968730B2

Reaction notes

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