5-Hydroxyindole → HCID 9926502, compound

HRID 1016291Notes

Reaction equation

HRID 1016291 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[CH:5]2.[CH2:11]([N:18]1[CH2:23][CH2:22][C:21](=O)[CH2:20][CH2:19]1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>C(O)(=O)C>[C:12]1([CH2:11][N:18]2[CH2:19][CH:20]=[C:21]([C:5]3[C:4]4[C:8](=[CH:9][CH:10]=[C:2]([OH:1])[CH:3]=4)[NH:7][CH:6]=3)[CH2:22][CH2:23]2)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

4

Reactant 2

HCID 160545-HydroxyindoleHCID 192201-Benzyl-4-piperidone

Product 1

HCID 9926502HCID 9926502, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of 5-hydroxyindole (0.66 g) and 1-benzyl-4-piperidone (0.95 g) in glacial acetic acid was purged with nitrogen and heated to reflux for 50 min. The mixture was concentrated in vacuo, treated with toluene and concentrated in vacuo, and the residue was purified by chromatography (silica gel, 20-30% ethanol/dichloromethane) to afford the title compound which was recrystallized from ethanol (0.4 g). mp 223-227° C.

Workup

  1. customwas purged with nitrogen
  2. temperatureheated
  3. temperatureto reflux for 50 min
  4. concentrationThe mixture was concentrated in vacuo
  5. additiontreated with toluene
  6. concentrationconcentrated in vacuo
  7. customthe residue was purified by chromatography (silica gel, 20-30% ethanol/dichloromethane)

Sources & evidence

ORD record
ord-13da8b0bf9454572b661ffa3cb267ccb
Source dataset
uspto-grants-2002_11
Patent number
US06476028B1

Reaction notes

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