Formaldehyde → HCID 21270035, compound

HRID 1194353Notes

Reaction equation

HRID 1194353 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH3:11])[CH:6]=[C:5]2[C:12](=[O:14])[CH3:13].[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:5]1[C:4]2[C:8](=[CH:9][CH:10]=[C:2]([F:1])[CH:3]=2)[N:7]([CH3:11])[CH:6]=1)=[O:14]

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 10473Dimethylamine, hydrochlorideHCID 16751083HCID 16751083, compound

Product 1

HCID 21270035HCID 21270035, compoundYield 41%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 1-(5-fluoro-1-methyl-1H-indol-3-yl)-1-ethanone (0.9 g) in ethanol (60 ml) containing paraformaldehyde (0.45 g) and dimethylamine hydrochloride (1.2 g) was heated at reflux for 18 h, cooled, and the solvent was evaporated in vacuo. The residue was partitioned between sodium carbonate (2N; 100 ml) and ethyl acetate (2×100 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 (0.55 g). A sample (0.1 g) was dissolved in absolute ethanol (5 ml) acidified with ethanolic hydrogen chloride, and the salt was precipitated by the addition of dry ether (ca. 150 ml). The salt was filtered off, and dried in vacuo to give the title compound (0.1 g), m.p. 184°-185°.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 18 h
  3. temperaturecooled
  4. customthe solvent was evaporated in vacuo
  5. customThe residue was partitioned between sodium carbonate (2N; 100 ml) and ethyl acetate (2×100 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-3be2a7279e7d46d1b1b3864ac5b3dbd0
Source dataset
uspto-grants-1989_03
Patent number
US04814344

Reaction notes

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