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

HRID 2165644Notes

Reaction equation

HRID 2165644 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 cooled 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. temperaturecooled to 0°-5° C. under argon
  2. temperatureThe temperature was maintained at 0°-5° C. until solution
  3. customrecooled to 0°-5° C.
  4. stirringThis mixture was stirred for 18 hours
  5. customthe mixture evaporated to dryness in vacuo
  6. dissolutionThe residue was dissolved in dichloromethane
  7. washwashed with water
  8. customdried
  9. filtrationfiltered
  10. customevaporated
  11. customgiving an oil, which
  12. filtrationfiltered
  13. concentrationconcentrated in vacuo at 40° C
  14. customThe solid was collected
  15. washwashed with cold ether
  16. customdried

Sources & evidence

ORD record
ord-ef17fb62631b48b9b93c98176d9a874f
Source dataset
uspto-grants-1990_07
Patent number
US04940710

Reaction notes

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