1-(2-Hydroxyethyl)piperazine → 2-[4-(2-hydroxyethyl)piperazin-1-yl]-1-phenyl-1H-indole-3-carboxaldehyde

HRID 1678116Notes

Reaction equation

HRID 1678116 reaction equation
Cl[C:2]1[N:3]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[C:4]2[C:9]([C:10]=1[CH:11]=[O:12])=[CH:8][CH:7]=[CH:6][CH:5]=2.[OH:19][CH2:20][CH2:21][N:22]1[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]1>O1CCOCC1.O>[OH:19][CH2:20][CH2:21][N:22]1[CH2:27][CH2:26][N:25]([C:2]2[N:3]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[C:4]3[C:9]([C:10]=2[CH:11]=[O:12])=[CH:8][CH:7]=[CH:6][CH:5]=3)[CH2:24][CH2:23]1

Participants

5

Reactant 2

HCID 76771-(2-Hydroxyethyl)piperazineHCID 3147932-chloro-1-phenyl-1H-indole-3-carbaldehyde

Product 1

HCID 111755082-[4-(2-hydroxyethyl)piperazin-1-yl]-1-phenyl-1H-indole-3-carboxaldehyde

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

2-Chloro-1-phenyl-1H-indole-3-carboxaldehyde (2.55 g, 19.6 mmol), 4-(2-hydroxyethyl)-piperazine (1.00 g, 3.92 mmol) in dioxane (13 mL) is heated overnight at reflux. The cooled reaction is diluted with water and extracted with dichloromethane. The organic layer is dried, filtered and evaporated to a semi-solid that is triturated with ether to give the 2-[4-(2-hydroxyethyl)piperazin-1-yl]-1-phenyl-1H-indole-3-carboxaldehyde as a brownish solid. MS 350 (M+H).

Workup

  1. temperatureat reflux
  2. customThe cooled reaction
  3. extractionextracted with dichloromethane
  4. customThe organic layer is dried
  5. filtrationfiltered
  6. customevaporated to a semi-solid
  7. customthat is triturated with ether

Sources & evidence

ORD record
ord-b4d592ccdc10492ba67ed17243410493
Source dataset
uspto-grants-2011_08
Patent number
US08008491B2

Reaction notes

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