Sodium Hydroxide → HCID 20244036, compound

HRID 482867Notes

Reaction equation

HRID 482867 reaction equation
[ClH:1].C([O:5][C:6]1[CH:7]=[C:8]2[C:12](=[CH:13][CH:14]=1)[N:11]([CH:15]([CH3:17])[CH3:16])[C:10]([CH3:18])=[C:9]2[C:19]([NH:21][CH:22]1[CH2:27][CH2:26][N:25]([CH2:28][CH2:29][C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[CH2:24][CH2:23]1)=[O:20])(=O)C.[OH-].[Na+]>CO.O>[ClH:1].[OH:5][C:6]1[CH:7]=[C:8]2[C:12](=[CH:13][CH:14]=1)[N:11]([CH:15]([CH3:16])[CH3:17])[C:10]([CH3:18])=[C:9]2[C:19]([NH:21][CH:22]1[CH2:23][CH2:24][N:25]([CH2:28][CH2:29][C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[CH2:26][CH2:27]1)=[O:20]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 20244025HCID 20244025, compound

Product 1

HCID 20244036HCID 20244036, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a solution of a total amount of the hydrochloride in 80 ml of methanol was added a solution of 2 g of sodium hydroxide in 10 ml of water, and the mixture was stirred for 10 minutes. After the methanol was concentrated, water was added to the residue to separate oil. To the oil was added 3 ml of glacial acetic acid and ethyl acetate, and the mixture was shaken well. The organic layer was washed with water and an aqueous solution of sodium hydrogencarbonate and the precipitated crystals were filtered. The crystals were dissolved in acetone containing ethanol and treated with concentrated hydrochloric acid to precipitate the corresponding hydrochloride. The crystalline hydrochloride was filtered and recrystallized from aqueous ethanol to give 5-hydroxy-1-isopropyl-2-methyl-N-(1-(2-phenylethyl)-4-piperidyl)indole-3-carboxamide hydrochloride, melting at 271°-276° C. with decomposition.

Workup

  1. concentrationAfter the methanol was concentrated
  2. additionwater was added to the residue
  3. customto separate oil
  4. additionTo the oil was added 3 ml of glacial acetic acid and ethyl acetate
  5. stirringthe mixture was shaken well
  6. washThe organic layer was washed with water
  7. filtrationan aqueous solution of sodium hydrogencarbonate and the precipitated crystals were filtered
  8. dissolutionThe crystals were dissolved in acetone
  9. additioncontaining ethanol
  10. additiontreated with concentrated hydrochloric acid
  11. customto precipitate the corresponding hydrochloride
  12. filtrationThe crystalline hydrochloride was filtered
  13. customrecrystallized from aqueous ethanol

Sources & evidence

ORD record
ord-2b5ec4fb62d54e788ca15905c05af5d7
Source dataset
uspto-grants-1986_03
Patent number
US04576940

Reaction notes

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