Acetic Acid → (5-methoxy-4-methyl-1H-indol-3-ylmethyl)dimethylamine

HRID 6744

Reaction equation

HRID 6744 reaction equation
[C:1](O)(=O)C.[CH3:5][NH:6][CH3:7].C=O.[CH3:10][O:11][C:12]1[C:13]([CH3:21])=[C:14]2[C:18](=[CH:19][CH:20]=1)[NH:17][CH:16]=[CH:15]2>C(O)C>[CH3:10][O:11][C:12]1[C:13]([CH3:21])=[C:14]2[C:7](=[CH:19][CH:20]=1)[NH:6][CH:5]=[C:15]2[CH2:16][N:17]([CH3:1])[CH3:18]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 674DimethylamineHCID 712FormaldehydeHCID 32962425-Methoxy-4-methylindole

Product 1

HCID 22018474(5-methoxy-4-methyl-1H-indol-3-ylmethyl)dimethylamine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

Acetic acid (0.39 mL) and dimethylamine (0.85 mL of a 40% aqueous solution) were added to a suspension of paraformaldehyde (0.21 g) in 25 mL ethanol. The mixture was heated to reflux until it was clear. The solution was cooled to rt and a solution of 5-methoxy-4-methyl-indole (1.0 g) in 25 mL of ethanol was added. The reaction was heated to reflux for 3 h. The volatiles were removed in vacuo to yield (5-methoxy-4-methyl-1H-indol-3-ylmethyl)-dimethylamine (1.0 g).

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux until it
  3. temperatureThe reaction was heated
  4. temperatureto reflux for 3 h
  5. customThe volatiles were removed in vacuo

Sources & evidence

ORD record
ord-cb0d67a099774221b16872d3e7d1a7ba
Source dataset
uspto-grants-2006_08
Patent number
US07084154B2

Linked notes

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