Thiirane → HCID 86609047, compound

HRID 1392034Notes

Reaction equation

HRID 1392034 reaction equation
[NH:1]1[C:9]2[C:4](=[C:5]([N:10]3[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]3)[CH:6]=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.[S:16]1[CH2:18][CH2:17]1>CN(C=O)C>[NH:1]1[C:9]2[C:4](=[C:5]([N:10]3[CH2:15][CH2:14][N:13]([CH2:18][CH2:17][SH:16])[CH2:12][CH2:11]3)[CH:6]=[CH:7][CH:8]=2)[CH:3]=[CH:2]1

Participants

4

Reactant 2

HCID 9865ThiiraneHCID 5945904-(piperazin-1-yl)-1H-indole

Product 1

HCID 86609047HCID 86609047, compoundYield 43.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1-(1H-Indol-4-yl)piperazine (3.9 g) and thiirane (1.75 g) was dissolved in DMF (200 mL) and refluxed for 1 h. The mixture was evaporated and re-dissolved in TBF, dried with MgSO4, filtered and evaporated to give the an oil which was subjected to purification by column chromatography (silica gel; ethyl acetate and heptane) giving the title compound as an oil (2,2 g). MS m/z (%): 261 (MH+, 100%), 202 (100%), 159 (23%).

Workup

  1. temperaturerefluxed for 1 h
  2. customThe mixture was evaporated
  3. dissolutionre-dissolved in TBF
  4. dry with materialdried with MgSO4
  5. filtrationfiltered
  6. customevaporated
  7. customto give the an oil which
  8. customwas subjected to purification by column chromatography (silica gel; ethyl acetate and heptane)

Sources & evidence

ORD record
ord-d94be4617f2644139e61516bde9a76e5
Source dataset
uspto-grants-2008_03
Patent number
US07342015B2

Reaction notes

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