Potassium Hydroxide → HCID 131316, compound

HRID 482864Notes

Reaction equation

HRID 482864 reaction equation
Cl.C([O:5][C:6]1[CH:7]=[C:8]2[C:12](=[CH:13][CH:14]=1)[N:11]([CH2:15][CH2:16][CH2:17][CH3:18])[C:10]([CH3:19])=[C:9]2[C:20]([NH:22][CH:23]1[CH2:28][CH2:27][N:26]([CH2:29][CH2:30][C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[CH2:25][CH2:24]1)=[O:21])(=O)C.[OH-].[K+]>CO>[CH2:15]([N:11]1[C:12]2[C:8](=[CH:7][C:6]([OH:5])=[CH:14][CH:13]=2)[C:9]([C:20]([NH:22][CH:23]2[CH2:24][CH2:25][N:26]([CH2:29][CH2:30][C:31]3[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=3)[CH2:27][CH2:28]2)=[O:21])=[C:10]1[CH3:19])[CH2:16][CH2:17][CH3:18]

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 20244007HCID 20244007, compound

Product 1

HCID 131316HCID 131316, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

To a solution of 2.3 g of 5-acetoxy-1-butyl-2-methyl-N-(1-(2-phenylethyl)-4-piperidyl)indole-3-carboxamide hydrochloride in 30 ml of methanol was added a solution of 0.5 g of potassium hydroxide in methanol, and the whole solution was stirred for an hour under heating. After the reaction mixture was cooled, the precipitated inorganic substance was filtered off and the filtrate was concentrated under reduced pressure. A solution of the residue in water with a small amount of ethanol was stirred and the precipitated crystals were filtered with suction. Recrystallization from ethyl acetate gave 1-butyl-5-hydroxy-2-methyl-N-(1-(2-phenylethyl)-4-piperidyl)indole-3-carboxamide as white crystals, melting at 178°-181° C. The corresponding hydrochloride monohydrate melts at 244°-247° C. with decomposition.

Workup

  1. temperatureunder heating
  2. temperatureAfter the reaction mixture was cooled
  3. filtrationthe precipitated inorganic substance was filtered off
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. stirringA solution of the residue in water with a small amount of ethanol was stirred
  6. filtrationthe precipitated crystals were filtered with suction
  7. customRecrystallization from ethyl acetate

Sources & evidence

ORD record
ord-84a4e70380a8456482d0b75874c599e9
Source dataset
uspto-grants-1986_03
Patent number
US04576940

Reaction notes

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