1-Iodopentane → HCID 3055740, compound

HRID 1277647Notes

Reaction equation

HRID 1277647 reaction equation
[CH2:1](I)[CH2:2][CH2:3][CH2:4][CH3:5].[NH:7]1[CH2:12][CH:11]=[C:10]([C:13]2[C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[NH:15][CH:14]=2)[CH2:9][CH2:8]1>CC(C)=O.[Ag]=O>[CH2:1]([N:7]1[CH2:8][CH:9]=[C:10]([C:13]2[C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[NH:15][CH:14]=2)[CH2:11][CH2:12]1)[CH2:2][CH2:3][CH2:4][CH3:5]

Participants

5

Reactant 2

HCID 123351-Iodopentane2×HCID 27610233-(1,2,3,6-Tetrahydropyridin-4-yl)-1H-indole

Product 1

HCID 3055740HCID 3055740, compound

Reagents, catalysts & solvents 2

HCID 92152Silver(II) oxideCatalystHCID 180AcetoneSolvent

Procedure

5.18 g of silver oxide and then 20 ml of pentyl iodide were added to a solution of 10 g of 3-(1,2,3,6-tetrahydropyridin-4yl)-1H-indole in 100 ml of acetone and after stirring the mixture for 4 hours at room temperature, another 2.5 ml of pentyl iodide were added thereto. The mixture was stirred for one hour and was filtered and the filter was rinsed with a 1-1 methylene chloride-methanol mixture. The filtrate was evaporated to dryness under reduced pressure at 40° C. and the residue was chromatographed over silica gel. Elution was effected with a 7-2-1 chloroform-methanol-triethylamine mixture and the residue from evaporation of the solvents was extracted with 250 ml of refluxing ethanol. The organic extract was filtered and crystallization of the filtrate was effected at 0° to 5° C. to obtain 7.9 g of 3-(1-pentyl-1,2,3,6-tetrahydropyridin-4-yl)-1H-indole melting at about 180° C.

Workup

  1. stirringThe mixture was stirred for one hour
  2. filtrationwas filtered
  3. washthe filter was rinsed with a 1-1 methylene chloride-methanol mixture
  4. customThe filtrate was evaporated to dryness under reduced pressure at 40° C.
  5. customthe residue was chromatographed over silica gel
  6. washElution
  7. customthe residue from evaporation of the solvents
  8. extractionwas extracted with 250 ml of refluxing ethanol
  9. extractionThe organic extract
  10. filtrationwas filtered
  11. customcrystallization of the filtrate
  12. customwas effected at 0° to 5° C.

Sources & evidence

ORD record
ord-b9ba98d32c1148ef8d5c8ccd51ce0066
Source dataset
uspto-grants-1981_07
Patent number
US04278677

Reaction notes

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