Formaldehyde → 3-(Dimethylamino)-1-(1,5-dimethyl-1H-indol-3-yl)-1-propanone hydrochloride

HRID 1194351Notes

Reaction equation

HRID 1194351 reaction equation
[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][C:7]([CH3:11])=[CH:8][CH:9]=2)[C:4]([C:12](=[O:14])[CH3:13])=[CH:3]1.[CH2:15]=O.[ClH:17].[CH3:18][NH:19][CH3:20]>C(O)C>[ClH:17].[CH3:18][N:19]([CH3:15])[CH2:20][CH2:13][C:12]([C:4]1[C:5]2[C:10](=[CH:9][CH:8]=[C:7]([CH3:11])[CH:6]=2)[N:2]([CH3:1])[CH:3]=1)=[O:14]

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 10473Dimethylamine, hydrochlorideHCID 212700661-(5-Methyl-1-methyl-1H-indol-3-YL)-ethanone

Product 1

HCID 212700693-(Dimethylamino)-1-(1,5-dimethyl-1H-indol-3-yl)-1-propanone hydrochlorideYield 38.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 1-(1,5-dimethyl-1H-indol-3-yl)-1-ethanone (1.4 g), paraformaldehyde (0.7 g) and dimethylamine hydrochloride (1.8 g) in ethanol (60 ml) was heated at reflux for 24 h, cooled, and the solvent was evaporated in vacuo. The residue was partitioned between sodium carbonate (2N; 75 ml) and ethyl acetate (2×75 ml). The combined organic extracts were dried and evaporated in vacuo to give an oil, which was purified by FCC eluting with System A to give the free base of the title compound as an oil (0.8 g). A sample of the free base (0.1 g) was dissolved in hot ethanol (10 ml) acidified with ethanolic hydrogen chloride, and diluted with hot ethyl acetate (40 ml). On cooling, the salt crystallised out and was filtered off, and dried in vacuo to give the title compound (0.1 g), m.p. 225°-228°.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 24 h
  3. temperaturecooled
  4. customthe solvent was evaporated in vacuo
  5. customThe residue was partitioned between sodium carbonate (2N; 75 ml) and ethyl acetate (2×75 ml)
  6. customThe combined organic extracts were dried
  7. customevaporated in vacuo
  8. customto give an oil, which
  9. customwas purified by FCC
  10. washeluting with System A

Sources & evidence

ORD record
ord-41dc0f7b3ba64c90954915daa10de3e3
Source dataset
uspto-grants-1989_03
Patent number
US04814344

Reaction notes

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