Dimethylformamide → HCID 3055742, compound

HRID 1277651Notes

Reaction equation

HRID 1277651 reaction equation
[CH3:1][O:2][C:3]1[CH:11]=[C:10]2[C:6]([C:7]([C:12]3[CH2:13][CH2:14][NH:15][CH2:16][CH:17]=3)=[CH:8][NH:9]2)=[CH:5][CH:4]=1.CN(C)C=O.C(=O)([O-])[O-].[Na+].[Na+].[CH2:29](I)[CH2:30][CH3:31]>O>[CH3:1][O:2][C:3]1[CH:11]=[C:10]2[C:6]([C:7]([C:12]3[CH2:13][CH2:14][N:15]([CH2:29][CH2:30][CH3:31])[CH2:16][CH:17]=3)=[CH:8][NH:9]2)=[CH:5][CH:4]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 10340Sodium CarbonateHCID 336431-IodopropaneHCID 130190056-methoxy-3-(1,2,3,6-tetrahydropyridin-4-yl)-1H-indole

Product 1

HCID 3055742HCID 3055742, compoundYield 83.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 10 g of the product of Step A, 200 ml of dimethylformamide, 9.28 g of sodium carbonate and 8.93 g of propyl iodide was stirred under an inert atmosphere for 5 hours and was then poured into 1.5 liters of water. The mixture was allowed to crystallize and was stirred for one hour and then vacuum filtered. The recovered product was rinsed with water and dried at 50° C. under reduced pressure in the presence of a dehydrating agent to obtain 9.9 g of 6-methoxy-3-(1-propyl-1,2,3,6-tetrahydropyridin-4-yl)-1H-indole melting at 219°-220° C.

Workup

  1. customto crystallize
  2. stirringwas stirred for one hour
  3. filtrationvacuum filtered
  4. washThe recovered product was rinsed with water
  5. customdried at 50° C. under reduced pressure in the presence of a dehydrating agent

Sources & evidence

ORD record
ord-b8e2292610f54f0586d1b46f38e7394e
Source dataset
uspto-grants-1981_07
Patent number
US04278677

Reaction notes

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