Acetonitrile → N-(1-hexylpiperidin-4-yl)xanthene-9-carboxamide

HRID 370270Notes

Reaction equation

HRID 370270 reaction equation
C(=O)([O-])[O-].[K+].[K+].I[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH3:13].C(#N)C.Cl.[NH:18]1[CH2:23][CH2:22][CH:21]([NH:24][C:25]([CH:27]2[C:40]3[CH:39]=[CH:38][CH:37]=[CH:36][C:35]=3[O:34][C:33]3[C:28]2=[CH:29][CH:30]=[CH:31][CH:32]=3)=[O:26])[CH2:20][CH2:19]1>O>[CH2:8]([N:18]1[CH2:19][CH2:20][CH:21]([NH:24][C:25]([CH:27]2[C:28]3[CH:29]=[CH:30][CH:31]=[CH:32][C:33]=3[O:34][C:35]3[C:40]2=[CH:39][CH:38]=[CH:37][CH:36]=3)=[O:26])[CH2:22][CH2:23]1)[CH2:9][CH2:10][CH2:11][CH2:12][CH3:13]

Participants

6

Reactant 4

HCID 6342AcetonitrileHCID 11430Potassium CarbonateHCID 125271-IodohexaneHCID 23283003N-(piperidin-4-yl)xanthene-9-carboxamide hydrochloride

Product 1

HCID 11794863N-(1-hexylpiperidin-4-yl)xanthene-9-carboxamide

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

60 mg of potassium carbonate and 25 ml of iodohexane were successively added to 5.0 ml of acetonitrile suspension having 50 mg of N-(piperidin-4-yl)xanthene-9-carboxamide hydrochloride, followed by reflux under heating for 4 hours. After cooled to room temperature, water was added to the reaction solution, followed by extraction with ethyl acetate and drying over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, the obtained residue was purified by preparative thin layer chromatography (Kieselgel™60F254, Art5744 produced by Merck Co.: chloroform/methanol=10/1), and 35 mg of the title compound as a white solid was obtained.

Workup

  1. temperatureby reflux
  2. temperatureunder heating for 4 hours
  3. extractionfollowed by extraction with ethyl acetate
  4. dry with materialdrying over anhydrous magnesium sulfate
  5. distillationThe solvent was distilled off under reduced pressure
  6. customthe obtained residue was purified by preparative thin layer chromatography (Kieselgel™60F254, Art5744 produced by Merck Co.: chloroform/methanol=10/1)

Sources & evidence

ORD record
ord-5d9b8530ec924490abf026fab400f5d0
Source dataset
uspto-grants-2000_10
Patent number
US06140338

Reaction notes

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