Formaldehyde → 3-(Dimethylamino)-1-(1-methyl-1H-indol-3-yl)propan-1-one

HRID 1194343Notes

Reaction equation

HRID 1194343 reaction equation
[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]([C:11](=[O:13])[CH3:12])=[CH:3]1.[CH2:14]=O.Cl.[CH3:17][NH:18][CH3:19]>C(O)C.O>[CH3:17][N:18]([CH3:14])[CH2:19][CH2:12][C:11]([C:4]1[C:5]2[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=2)[N:2]([CH3:1])[CH:3]=1)=[O:13]

Participants

6

Reactant 3

HCID 712FormaldehydeHCID 10473Dimethylamine, hydrochlorideHCID 5941561-(1-Methyl-1H-indol-3-yl)ethanone

Product 1

HCID 212700603-(Dimethylamino)-1-(1-methyl-1H-indol-3-yl)propan-1-oneYield 93.6%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A mixture of 1-(1-methyl-1H-indol-3-yl)-1-ethanone (46.16 g), paraformaldehyde (12.0 g) and dimethylamine hydrochloride (21.65 g) in ethanol (970 ml) was stirred and heated at reflux for 24 h. The mixture was diluted with water (3.5 l) and filtered. The filtrate was basified with 0.88 ammonia solution and extracted with ethyl acetate (3×665 ml). The combined organic extracts were washed with water, dried and evaporated to give title compound (57.24 g) as an oil, λmax (EtOH) 245.5 nm (ε15,820), λmax 303.5 nm (ε15,680), λinf 249.5 nm (ε15,015).

Workup

  1. temperatureheated
  2. temperatureat reflux for 24 h
  3. filtrationfiltered
  4. extractionextracted with ethyl acetate (3×665 ml)
  5. washThe combined organic extracts were washed with water
  6. customdried
  7. customevaporated

Sources & evidence

ORD record
ord-5aac2025ab084276a158e98c925b81ac
Source dataset
uspto-grants-1989_03
Patent number
US04814344

Reaction notes

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