Dimethylformamide → 1H-Indole, 5-chloro-3-(1-propyl-1,2,3,6-tetrahydro-4-pyridinyl)-, monohydrochloride

HRID 1277652Notes

Reaction equation

HRID 1277652 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+].[CH2:28](I)[CH2:29][CH3:30]>O>[ClH:1].[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]([CH2:28][CH2:29][CH3:30])[CH2:15][CH:16]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 10340Sodium CarbonateHCID 336431-IodopropaneHCID 30505325-chloro-3-(1,2,3,6-tetrahydropyridin-4-yl)-1H-indole

Product 1

HCID 30557471H-Indole, 5-chloro-3-(1-propyl-1,2,3,6-tetrahydro-4-pyridinyl)-, monohydrochlorideYield 112%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 9.28 g of 5-chloro-3-(1,2,3,6-tetrahydropyridin-4-yl)-1H-indole (prepared by the process of Belgium Pat. No. 858,101), 140 ml of dimethylformamide, 8.48 g of sodium carbonate and 4.67 g of propyl iodide was stirred for 5 hours at room temperature under an inert atmosphere and was then poured with stirring into 1.4 liters of water after which crystallization occured. The mixture was filtered and the recovered product was rinsed with water and dried under reduced pressure in the presence of a dehydrating agent. The product was crystallized from ethanol to obtain 6.95 g of 5-chloro-3-(1-propyl-1,2,3,6-tetrahydropyridin-4-yl)-1H-indole hydrochloride melting at 229°-230° C.

Workup

  1. customprepared by the process of Belgium Pat
  2. additionwas then poured
  3. customafter which crystallization
  4. filtrationThe mixture was filtered
  5. washthe recovered product was rinsed with water
  6. customdried under reduced pressure in the presence of a dehydrating agent
  7. customThe product was crystallized from ethanol

Sources & evidence

ORD record
ord-9c86e559e4bd4be998d1e1f3f1ad7528
Source dataset
uspto-grants-1981_07
Patent number
US04278677

Reaction notes

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