Potassium Hydroxide → HCID 20244002, compound

HRID 482865Notes

Reaction equation

HRID 482865 reaction equation
[OH-].[K+].[ClH:3].C([O:7][C:8]1[CH:9]=[C:10]2[C:14](=[CH:15][CH:16]=1)[N:13]([CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[C:12]([CH3:24])=[C:11]2[C:25]([NH:27][CH:28]1[CH2:33][CH2:32][N:31]([CH2:34][CH2:35][C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)[CH2:30][CH2:29]1)=[O:26])(=O)C>CO>[ClH:3].[CH2:17]([N:13]1[C:14]2[C:10](=[CH:9][C:8]([OH:7])=[CH:16][CH:15]=2)[C:11]([C:25]([NH:27][CH:28]2[CH2:29][CH2:30][N:31]([CH2:34][CH2:35][C:36]3[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=3)[CH2:32][CH2:33]2)=[O:26])=[C:12]1[CH3:24])[C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 20244032HCID 20244032, compound

Product 1

HCID 20244002HCID 20244002, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 7.6 g of potassium hydroxide in 500 ml of methanol was added 37 g of the hydrochloride obtained in Example 3, and the mixture was stirred at room temperature for 2 hours. The insoluble substance was filtered off and the filtrate was concentrated. To the residue was added 2 liters of water and the mixture was stirred, and then the precipitated crystals were filtered with suction. After the crystals were recrystallized from a mixture of ethyl acetate and methanol, 12.5 g of the purified crystals were redissolved in 350 ml of methanol under heating. To the solution was added 8 ml of 18% hydrochloric acid and the mixture was cooled with ice. The precipitated crystals were filtered with suction to give 1-benzyl-5-hydroxy-2-methyl-N-(1-(2-phenylethyl)-4-piperidyl)indole-3-carboxamide hydrochloride as white crystals, melting at 210°-212° C.

Workup

  1. filtrationThe insoluble substance was filtered off
  2. concentrationthe filtrate was concentrated
  3. additionTo the residue was added 2 liters of water
  4. stirringthe mixture was stirred
  5. filtrationthe precipitated crystals were filtered with suction
  6. customAfter the crystals were recrystallized from a mixture of ethyl acetate and methanol, 12.5 g of the purified crystals
  7. dissolutionwere redissolved in 350 ml of methanol
  8. temperatureunder heating
  9. additionTo the solution was added 8 ml of 18% hydrochloric acid
  10. temperaturethe mixture was cooled with ice
  11. filtrationThe precipitated crystals were filtered with suction

Sources & evidence

ORD record
ord-6c35a6823d164f939496bfd4a5c1d7e9
Source dataset
uspto-grants-1986_03
Patent number
US04576940

Reaction notes

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