Water → HCID 22611528, compound

HRID 843879Notes

Reaction equation

HRID 843879 reaction equation
[OH-].[K+].O.Cl.N1CCC(=O)CC1.[F:12][C:13]1[CH:36]=[CH:35][C:16]([C:17]([NH:19][C:20]2[CH:21]=[C:22]3[C:26](=[CH:27][CH:28]=2)[NH:25][CH:24]=[C:23]3[CH:29]2[CH2:34][CH2:33][NH:32][CH2:31][CH2:30]2)=[O:18])=[CH:15][CH:14]=1.O>CO>[F:12][C:13]1[CH:14]=[CH:15][C:16]([C:17]([NH:19][C:20]2[CH:21]=[C:22]3[C:26](=[CH:27][CH:28]=2)[NH:25][CH:24]=[C:23]3[C:29]2[CH2:34][CH2:33][NH:32][CH2:31][CH:30]=2)=[O:18])=[CH:35][CH:36]=1

Participants

6

Reactant 4

HCID 962WaterHCID 14797Potassium HydroxideHCID 2723901PiperonylamineHCID 22611370HCID 22611370, compound

Product 1

HCID 22611528HCID 22611528, compoundYield 47.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
20 °C

Procedure

To a solution of 5.8 gm (90 mMol) potassium hydroxide in 75 mL methanol were added 9.22 gm (60 mMol) 4-piperidone hydrochloride monohydrate followed by 7.8 gm (30 mMol) 5-(4-fluorobenzoyl)amino-3-(piperidin-4-yl)-1H-indole (Example 182A). This solution was stirred at reflux for 18 hours. The reaction mixture was cooled to ambient and then poured slowly into 150 mL water, maintaining the temperature of the solution at about 20° C. The resulting precipitate was filtered and recrystallized from ethanol to give 4.72 gm (47.2%) of the title compound as tan crystals. 0.725 gm of the material were crystallized again from ethanol to provide 0.241 gm light yellow crystals for analysis.

Workup

  1. temperatureat reflux for 18 hours
  2. temperatureThe reaction mixture was cooled to ambient and
  3. filtrationThe resulting precipitate was filtered
  4. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-2f39ca2fed154f448169fcbbbcf11281
Source dataset
uspto-grants-2002_04
Patent number
US06380201B1

Reaction notes

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