5-(4-Acetamidophenyl)-3-(1-Methylpiperidin-4-yl)-1H-Indole → 5-(4-Aminophenyl)-3-(1-Methylpiperidin-4-yl)-1H-Indole

HRID 278021Notes

Reaction equation

HRID 278021 reaction equation
C([NH:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]2[CH:12]=[C:13]3[C:17](=[CH:18][CH:19]=2)[NH:16][CH:15]=[C:14]3[CH:20]2[CH2:25][CH2:24][N:23]([CH3:26])[CH2:22][CH2:21]2)=[CH:7][CH:6]=1)(=O)C>C(O)C.Cl>[NH2:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]2[CH:12]=[C:13]3[C:17](=[CH:18][CH:19]=2)[NH:16][CH:15]=[C:14]3[CH:20]2[CH2:25][CH2:24][N:23]([CH3:26])[CH2:22][CH2:21]2)=[CH:7][CH:6]=1

Participants

4

Reactant 1

HCID 98412175-(4-Acetamidophenyl)-3-(1-Methylpiperidin-4-yl)-1H-Indole

Product 1

HCID 120418105-(4-Aminophenyl)-3-(1-Methylpiperidin-4-yl)-1H-IndoleYield 52%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 702EthanolSolvent

Procedure

A solution of 5-(4-acetamido phenyl)-3-(1-methylpiperidin-4-yl)-1H-indole (0.150 g, 0.43 mmol) in 2 mL of ethanol and 1 mL of 1N aqueous hydrochloric acid solution was heated with stirring overnight. The mixture was allowed to cool to room temperature, solvent was removed in vacuo, and the residue was dissolved in 2N aqueous sodium hydroxide solution and ethyl acetate. The organic layer was separated, extracted with 2N aqueous sodium hydroxide solution followed by brine, dried over sodium sulfate, filtered, concentrated and purified by silica gel (flash) chromatography to give the title compound (0.068 g, 52%) as an amorphous yellow solid. FDMS m/e=305 (M+). EA calculated for C20H23N3: C, 78.65; H, 7.59; N, 13.76. Found: C, 78.42; H, 7.71; N, 13.57.

Workup

  1. customsolvent was removed in vacuo
  2. dissolutionthe residue was dissolved in 2N aqueous sodium hydroxide solution
  3. customThe organic layer was separated
  4. extractionextracted with 2N aqueous sodium hydroxide solution
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. custompurified by silica gel (flash) chromatography

Sources & evidence

ORD record
ord-342819bea30a409798e78fa5392a71de
Source dataset
uspto-grants-2002_03
Patent number
US06358972B1

Reaction notes

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