Acetic Acid → N,N-Dimethyl-1-(2-methyl-1H-indol-3-yl)methanamine

HRID 224890Notes

Reaction equation

HRID 224890 reaction equation
[CH3:1][C:2](O)=O.C=O.[CH3:7][NH:8][CH3:9].[CH3:10][C:11]1[NH:12][C:13]2[C:18](C=1)=[CH:17][CH:16]=[CH:15][CH:14]=2>O1CCOCC1.O>[CH3:10][C:11]1[NH:12][C:13]2[C:18](=[CH:17][CH:16]=[CH:15][CH:14]=2)[C:2]=1[CH2:1][N:8]([CH3:9])[CH3:7]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 674DimethylamineHCID 712FormaldehydeHCID 72242-Methylindole

Product 1

HCID 181513N,N-Dimethyl-1-(2-methyl-1H-indol-3-yl)methanamine

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

AcOH, 236 ml., was mixed with cooling and stirring with 62 m. of 37% formaldehyde at 10°, and 154 ml of 25% aqueous dimethylamine was added dropwise with cooling so as to maintain the temperature at 10°. A solution of 100 g of 2-methylindole in 160 ml of dioxane was then added dropwise with cooling, again maintaining the temperature at 10°. The mixture was stirred at ice temperature for 1 hour and then overnight at room temperature. The mixture was then poured into 2.0 of water with stirring. A small amount of insoluble material was removed by filtration. The filtrate was treated with activated charcoal, filtered again, and the filtrate cooled and basified by the dropwise addition of about 225 ml. of 50% aqueous sodium hydroxide. The product was collected by filtration, washed with water, and air dried, yield 96 g. This material was dissolved in 700 ml of dilute aqueous HCl, treated with activated carbon, filtered, and again basified after diluting to 2 l. with water. The product was collected, air dried, and recrystallized from acetonitrile, yield 72 g., m.p. 117°-119°.

Workup

  1. addition, was mixed
  2. temperaturewith cooling
  3. temperaturewith cooling so as
  4. temperatureto maintain the temperature at 10°
  5. temperaturewith cooling
  6. temperatureagain maintaining the temperature at 10°
  7. stirringThe mixture was stirred at ice temperature for 1 hour
  8. customovernight
  9. customat room temperature
  10. stirringwith stirring
  11. customA small amount of insoluble material was removed by filtration
  12. additionThe filtrate was treated with activated charcoal
  13. filtrationfiltered again
  14. temperaturethe filtrate cooled
  15. additionbasified by the dropwise addition of about 225 ml
  16. filtrationThe product was collected by filtration
  17. washwashed with water, and air
  18. customdried
  19. dissolutionThis material was dissolved in 700 ml of dilute aqueous HCl
  20. additiontreated with activated carbon
  21. filtrationfiltered
  22. additionafter diluting to 2 l
  23. customThe product was collected
  24. customair dried
  25. customrecrystallized from acetonitrile, yield 72 g

Sources & evidence

ORD record
ord-19f19ddda9b9462587414516fe7df6c4
Source dataset
uspto-grants-1980_11
Patent number
US04234595

Reaction notes

Loading…