Dimethylformamide → HCID 12879206, compound

HRID 1277653Notes

Reaction equation

HRID 1277653 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[C:5]2[C:11]1[CH2:12][CH2:13][NH:14][CH2:15][CH:16]=1.CN(C)C=O.C(=O)([O-])[O-].[Na+].[Na+].[CH:28]1([CH2:31]Cl)[CH2:30][CH2:29]1>C(O)C.O>[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[C:5]2[C:11]1[CH2:12][CH2:13][N:14]([CH2:31][CH:28]2[CH2:30][CH2:29]2)[CH2:15][CH:16]=1

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 10340Sodium CarbonateHCID 80013(Chloromethyl)cyclopropaneHCID 30505325-chloro-3-(1,2,3,6-tetrahydropyridin-4-yl)-1H-indole

Product 1

HCID 12879206HCID 12879206, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of 12.5 g of 5-chloro-3-(1,2,3,6-tetrahydropyridin-4-yl)-1H-indole, 120 ml of anhydrous dimethylformamide, 11.5 g of sodium carbonate and 6.5 ml of cyclopropylmethyl chloride was stirred for 24 hours under an inert atmosphere at 70° C. and was then cooled to 30° C. after which 300 ml of distilled water were added thereto while cooling in an ice bath. Precipitation occured and the mixture was stirred for 45 minutes, stood for 15 minutes and was then filtered. The product was washed 3 times with distilled water and was empasted with 20 ml of 50% aqueous ethanol. The product was dried at 50° C. under reduced pressure in the presence of a dehydrating agent to obtain 13.54 g of raw product which was dissolved in 350 ml of refluxing ethanol. The solution was filtered and the filtrate was concentrated to 300 ml for crystallization. The solution was cooled to room temperature and was held in a refrigerator for 90 minutes. The mixture was vacuum filtered and the product was rinsed with ethanol and dried under reduced pressure to obtain 7.8 g of 5-chloro-3-(1-cyclopropylmethyl-1,2,3,6-tetrahydropyridin-4-yl)-1H-indole melting at 205° C.

Workup

  1. additionwere added
  2. temperaturewhile cooling in an ice bath
  3. customPrecipitation
  4. stirringthe mixture was stirred for 45 minutes
  5. waitstood for 15 minutes
  6. filtrationwas then filtered
  7. washThe product was washed 3 times with distilled water
  8. customThe product was dried at 50° C. under reduced pressure in the presence of a dehydrating agent
  9. customto obtain 13.54 g of raw product which
  10. filtrationThe solution was filtered
  11. concentrationthe filtrate was concentrated to 300 ml for crystallization
  12. temperatureThe solution was cooled to room temperature
  13. waitwas held in a refrigerator for 90 minutes
  14. filtrationfiltered
  15. washthe product was rinsed with ethanol
  16. customdried under reduced pressure

Sources & evidence

ORD record
ord-85ee958eb6ec4644a0d0948a63da559c
Source dataset
uspto-grants-1981_07
Patent number
US04278677

Reaction notes

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