Water → 1-(phenylsulfonyl)-3-(2-piperazinyl)-1H-indole

HRID 248495Notes

Reaction equation

HRID 248495 reaction equation
[C:1]([C:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[N:6]([S:13]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)(=[O:15])=[O:14])[CH:5]=1)(=O)[CH3:2].[CH2:22]([NH2:25])[CH2:23][NH2:24].[BH4-].[Na+].O>C(O)C.O1CCOCC1.CCOCC>[C:16]1([S:13]([N:6]2[C:7]3[C:12](=[CH:11][CH:10]=[CH:9][CH:8]=3)[C:4]([CH:1]3[CH2:2][NH:25][CH2:22][CH2:23][NH:24]3)=[CH:5]2)(=[O:15])=[O:14])[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

8

Reactant 4

HCID 962WaterHCID 3301EthylenediamineHCID 8485351H-Indole, 3-acetyl-1-(phenylsulfonyl)-HCID 4311764Sodium borohydride

Product 1

HCID 197635511-(phenylsulfonyl)-3-(2-piperazinyl)-1H-indoleYield 25.4%

Reagents, catalysts & solvents 3

HCID 702EthanolSolvent2×HCID 3283Diethyl EtherSolventHCID 312751,4-DioxaneSolvent

Procedure

The 19.1 g of the above indole derivative in 500 ml of ethanol and 200 ml of dioxane was stirred and cocled to 0°-5° C. under argon. A solution of 3.46 g of ethylenediamine in 100 ml of ethanol was added dropwise. The temperature was maintained at 0°-5° C. until solution was complete, then the mixture was stirred at room temperature for 3.5 hours, recooled to 0°-5° C. and 4.37 g of sodium borohydride added. This mixture was stirred for 18 hours, water was added and the mixture evaporated to dryness in vacuo. The residue was dissolved in dichloromethane, washed with water, dried, filtered and evaporated giving an oil, which solidified. The solid was dissolved in cold ether, filtered and concentrated in vacuo at 40° C. The solid was collected, washed with cold ether and dried, giving 5 g of 1-(phenylsulfonyl)-3-(2-piperazinyl)-1H-indole.

Workup

  1. temperatureThe temperature was maintained at 0°-5° C. until solution
  2. customrecooled to 0°-5° C.
  3. stirringThis mixture was stirred for 18 hours
  4. customthe mixture evaporated to dryness in vacuo
  5. dissolutionThe residue was dissolved in dichloromethane
  6. washwashed with water
  7. customdried
  8. filtrationfiltered
  9. customevaporated
  10. customgiving an oil, which
  11. filtrationfiltered
  12. concentrationconcentrated in vacuo at 40° C
  13. customThe solid was collected
  14. washwashed with cold ether
  15. customdried

Sources & evidence

ORD record
ord-a83cb6f449504a9b973e3efe9f6a95e1
Source dataset
uspto-grants-1993_05
Patent number
US05210193

Reaction notes

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