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Hydrochloric Acid → 1-Phenyl-3-(piperidin-4-yl)imidazolidin-2-one

HRID 614372
Notes
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Reaction equation

HRID 614372 reaction equation
C([N:8]1[CH2:13][CH2:12][CH:11]([N:14]2[CH2:18][CH2:17][N:16]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[C:15]2=[O:25])[CH2:10][CH2:9]1)C1C=CC=CC=1.O.Cl.[H][H]>CO.[Pd]>[NH:8]1[CH2:9][CH2:10][CH:11]([N:14]2[CH2:18][CH2:17][N:16]([C:19]3[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=3)[C:15]2=[O:25])[CH2:12][CH2:13]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 155726681-(1-Benzylpiperidin-4-yl)-3-phenylimidazolidin-2-oneHCID 178418361HCID 178418361, compound

Product 1

HCID 205401631-Phenyl-3-(piperidin-4-yl)imidazolidin-2-oneYield 93.6%

Reagents, catalysts & solvents 2

HCID 23938
Palladium
Catalyst
HCID 887MethanolSolvent

Procedure

11.1 g of 1-(1-benzyl-4-piperidinyl)-3-phenyl-2-imidazolidinone are dissolved in 85 ml of methanol, 34 ml of water and 3.2 ml of hydrochloric acid (chemically pure), and, with the addition of 1.2 g of a 5% palladium on charcoal catalyst, hydrogenated at room temperature and under normal pressure. The calculated amount of hydrogen has been taken up after approx. 15 hours. The reaction mixture is filtered to remove the catalyst and concentrated in a water jet vacuum. The crystalline residue is treated with 2N sodium carbonate solution and extracted with chloroform. The combined chloroform extracts are dried over sodium sulphate and concentrated in a water jet vacuum to yield 7.6 g of 1-(4-piperidinyl)-3-phenyl-2-imidazolidinone as a colourless oil which crystallises on standing; melting point 123°-124° C.

Workup

  1. customhydrogenated at room temperature
  2. filtrationThe reaction mixture is filtered
  3. customto remove the catalyst
  4. concentrationconcentrated in a water jet vacuum
  5. additionThe crystalline residue is treated with 2N sodium carbonate solution
  6. extractionextracted with chloroform
  7. dry with materialThe combined chloroform extracts are dried over sodium sulphate
  8. concentrationconcentrated in a water jet vacuum

Sources & evidence

ORD record
ord-dc91ae9a1a864f0ab12319d18cd38383
Source dataset
uspto-grants-1979_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04144344

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes