Dimethylformamide → HCID 3239482, compound

HRID 1277649Notes

Reaction equation

HRID 1277649 reaction equation
[NH:1]1[CH2:6][CH:5]=[C:4]([C:7]2[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[NH:9][CH:8]=2)[CH2:3][CH2:2]1.CN(C)C=O.C(=O)([O-])[O-].[Na+].[Na+].I[CH:28]([CH3:30])[CH3:29]>O>[CH:28]([N:1]1[CH2:2][CH:3]=[C:4]([C:7]2[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[NH:9][CH:8]=2)[CH2:5][CH2:6]1)([CH3:30])[CH3:29]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 6362Isopropyl iodideHCID 10340Sodium CarbonateHCID 27610233-(1,2,3,6-Tetrahydropyridin-4-yl)-1H-indole

Product 1

HCID 3239482HCID 3239482, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 5 g of 3-(1,2,3,6-tetrahydropyridin-4-yl)-1H-indole, 50 ml of dimethylformamide, 5.25 g of sodium carbonate and 2.7 ml of 2-iodopropane were stirred under an inert atmosphere and the mixture was then added dropwise over 20 hours to 400 ml of water. The mixture was stirred for 30 minutes, was allowed to crystallize and was then vacuum filtered. The recovered product was washed and dried at 50° C. under reduced pressure to obtain 5.8 g of 3-(1-isopropyl-1,2,3,6-tetrahydropyridin-4-yl)-1H-indole melting at 178° C.

Workup

  1. stirringThe mixture was stirred for 30 minutes
  2. customto crystallize
  3. filtrationvacuum filtered
  4. washThe recovered product was washed
  5. customdried at 50° C. under reduced pressure

Sources & evidence

ORD record
ord-32fb37756c6e4d4992ea05cdcf040c23
Source dataset
uspto-grants-1981_07
Patent number
US04278677

Reaction notes

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