Hydrochloric Acid → HCID 12851454, compound

HRID 905027Notes

Reaction equation

HRID 905027 reaction equation
[CH2:1]([C:3]1[C:7]([C:8]2[NH:9][C:10]3[C:15]([C:16]=2[C:17](=[O:19])[CH3:18])=[CH:14][CH:13]=[CH:12][CH:11]=3)=[C:6]([CH3:20])[O:5][N:4]=1)[CH3:2].Cl.[CH3:22][NH:23][CH3:24].Cl.[CH2:26]=O>C(O)C>[CH3:22][N:23]([CH3:26])[CH2:24][CH2:18][C:17]([C:16]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[NH:9][C:8]=1[C:7]1[C:3]([CH2:1][CH3:2])=[N:4][O:5][C:6]=1[CH3:20])=[O:19]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 712FormaldehydeHCID 10473Dimethylamine, hydrochlorideHCID 128514531-[2-(3-Ethyl-5-methyl-1,2-oxazol-4-yl)-1H-indol-3-yl]ethan-1-one

Product 1

HCID 12851454HCID 12851454, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 12 g. (0.045 mole) of 2-(3-ethyl-5-methyl-4-isoxazolyl)-3-acetyl indole, 4 g. (0.049 mole) of dimethylamine hydrochloride, and 0.5 ml. concentrated hydrochloric acid in 70 ml. of ethanol is heated to reflux and treated by the portionwise addition of 14 g. (0.470 mole) of paraformaldehyde over 5 hours. The resulting mixture is refluxed an additional 24 hours, cooled and evaporated in vacuo. The residue is then dissolved in 300 ml. methylene chloride and washed with 200 ml. 2 N hydrochloric acid, the aqueous acid is cooled and made basic with 2 N sodium hydroxide and extracted with methylene chloride. The organic layer is dried over anhydrous magnesium sulfate, filtered and evaporated in vacuo. The residue is crystallized from ether to give 3-dimethylamino-1-[2-(3-ethyl-5-methyl-4-isoxazolyl)-1H-indol-3-yl]-1-propanone, m.p. 146°-148° C.

Workup

  1. additionA mixture of 12 g
  2. temperatureto reflux
  3. additiontreated by the portionwise addition of 14 g
  4. temperatureThe resulting mixture is refluxed an additional 24 hours
  5. temperaturecooled
  6. customevaporated in vacuo
  7. dissolutionThe residue is then dissolved in 300 ml
  8. washmethylene chloride and washed with 200 ml
  9. temperature2 N hydrochloric acid, the aqueous acid is cooled
  10. extractionextracted with methylene chloride
  11. dry with materialThe organic layer is dried over anhydrous magnesium sulfate
  12. filtrationfiltered
  13. customevaporated in vacuo
  14. customThe residue is crystallized from ether

Sources & evidence

ORD record
ord-486624e6ea2645f084e632e34b858190
Source dataset
uspto-grants-1983_12
Patent number
US04421752

Reaction notes

Loading…