Hydrochloric Acid → HCID 12915861, compound

HRID 543491Notes

Reaction equation

HRID 543491 reaction equation
[O:1]=[C:2]([C:21]1[CH:26]=[CH:25][CH:24]=[C:23]([O:27]CC2C=CC=CC=2)[CH:22]=1)[CH:3]([N:5]1[CH2:10][CH2:9][CH:8]([N:11]2[C:15]3[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=3[NH:13][C:12]2=[O:20])[CH2:7][CH2:6]1)[CH3:4].[ClH:35].[H][H]>CO.[C].[Pd]>[ClH:35].[OH:1][CH:2]([C:21]1[CH:26]=[CH:25][CH:24]=[C:23]([OH:27])[CH:22]=1)[CH:3]([N:5]1[CH2:10][CH2:9][CH:8]([N:11]2[C:15]3[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=3[NH:13][C:12]2=[O:20])[CH2:7][CH2:6]1)[CH3:4]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 12915854HCID 12915854, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 12915861HCID 12915861, compoundYield 88.6%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolvent2×

Procedure

0.7 g of 1-[3-oxo-3-(3-benzyloxyphenyl)-2-propyl]-4-(2-keto-1-benzimidazolinyl)-piperidine is dissolved in 50 ml of methanol, and 1 ml of methanol solution containing 0.1 g of hydrogen chloride is added thereto. Further, 0.2 g of palladium-carbon is added to the solution, and the mixture is shaked in an autoclave at room temperature with a hydrogen pressure of 10 atmospheric pressures to reduce the compound. After 24 hours, the reaction solution is subjected to filtration, and the mother liquor is concentrated under reduced pressure. Ethyl acetate is added to the residue, and filtered. The mixture is dried to obtain 0.55 g of 1-[3-hydroxy-(3-hydroxyphenyl)-2-propyl]-4-(2-keto-1-benzimidazolinyl)piperidine hydrochloride as powder.

Workup

  1. additionis added
  2. filtrationthe reaction solution is subjected to filtration
  3. concentrationthe mother liquor is concentrated under reduced pressure
  4. additionEthyl acetate is added to the residue
  5. filtrationfiltered
  6. customThe mixture is dried

Sources & evidence

ORD record
ord-a56056637c064375a1f990ed2f460ece
Source dataset
uspto-grants-1984_05
Patent number
US04446141

Reaction notes

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