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

HRID 751334

Reaction equation

HRID 751334 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-bdbbc4a1fb4b43aeab0b598183467d36
Source dataset
uspto-grants-2008_07
Patent number
US07405300B2

Linked notes

Loading…