Hydrochloric Acid → HCID 13490826, compound

HRID 2290204Notes

Reaction equation

HRID 2290204 reaction equation
C([N:8]1[CH2:13][CH2:12][CH:11]([NH:14][C:15]([C:17]2[C:25]3[C:20](=[CH:21][CH:22]=[C:23]([OH:26])[CH:24]=3)[N:19]([CH2:27][CH2:28][CH2:29][CH3:30])[C:18]=2[CH3:31])=[O:16])[CH2:10][CH2:9]1)C1C=CC=CC=1.[ClH:32]>CO.C(O)C.[C].[Pd]>[ClH:32].[CH2:27]([N:19]1[C:20]2[C:25](=[CH:24][C:23]([OH:26])=[CH:22][CH:21]=2)[C:17]([C:15]([NH:14][CH:11]2[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]2)=[O:16])=[C:18]1[CH3:31])[CH2:28][CH2:29][CH3:30]

Participants

6

Reactant 2

HCID 313Hydrochloric AcidHCID 13752624HCID 13752624, compound

Product 1

HCID 13490826HCID 13490826, compound

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 887MethanolSolventHCID 178418390HCID 178418390, compoundSolvent

Procedure

To a solution of 9 g of N-(1-benzyl-4-piperidyl)-1-butyl-5-hydroxy-2-methylindole-3-carboxamide in 100 ml of methanol were added 5 g of an 18% hydrochloric acid in ethanol and 4 g of 10% palladium carbon, and the mixture was subjected to catalytic hydrogenation at atmospheric pressure for 6 hours. After the catalyst was filtered off, the filtrate was concentrated under reduced pressure. The residue was crystallized with ethyl acetate and the resulting crystals were recrystallized from ethanol to give 4 g of 1-butyl-5-hydroxy-2-methyl-N-(4-piperidyl)indole-3-carboxamide hydrochloride, melting at 164°-168° C.

Workup

  1. filtrationAfter the catalyst was filtered off
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customThe residue was crystallized with ethyl acetate
  4. customthe resulting crystals were recrystallized from ethanol

Sources & evidence

ORD record
ord-8d61d89339d640e7b32ae79bccdbf350
Source dataset
uspto-grants-1986_10
Patent number
US04616009

Reaction notes

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