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Hydrochloric Acid → 3-(2-Hydroxyethyl)-1-(4-piperidyl)-imidazolidin-2-one

HRID 444454
Notes
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Reaction equation

HRID 444454 reaction equation
C([N:11]1[CH2:16][CH2:15][CH:14]([N:17]2[CH2:21][CH2:20][N:19]([CH2:22][CH2:23][O:24]C3CCCCO3)[C:18]2=[O:31])[CH2:13][CH2:12]1)(OCC1C=CC=CC=1)=O.Cl.[H][H]>CO.[Pd]>[OH:24][CH2:23][CH2:22][N:19]1[CH2:20][CH2:21][N:17]([CH:14]2[CH2:13][CH2:12][NH:11][CH2:16][CH2:15]2)[C:18]1=[O:31]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 23463795HCID 23463795, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 234638053-(2-Hydroxyethyl)-1-(4-piperidyl)-imidazolidin-2-one

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887
Methanol
Solvent

Procedure

A solution of 59.7 g of 1-(1-carbobenzoxy-4-piperidyl)-3-[2(2-tetrahydropyranyloxy)-ethyl]-imidazolidin-2-one in 1,200 ml of absolute methanol is hydrogenated at room temperature and normal pressure with the addition of 1 mol equivalent of hydrochloric acid and 6 g of palladium-on-charcoal catalyst until 2 mol equivalents of hydrogen have been taken up. The catalyst is then filtered off and the filtrate is evaporated under reduced pressure. The residue is freed from moisture which is still adhering, by treatment with toluene. The reaction product is chromatographed on 2 kg of basic aluminium oxide using a mixture of chloroform/methanol (85:15) as the eluant mixture. In this way, 3-(2-hydroxyethyl)-1-(4-piperidyl)-imidazolidin-2-one is obtained in the form of a viscous oil, which is further used without additional purification.

Workup

  1. customis hydrogenated at room temperature
  2. filtrationThe catalyst is then filtered off
  3. customthe filtrate is evaporated under reduced pressure
  4. customThe reaction product is chromatographed on 2 kg of basic aluminium oxide using
  5. additiona mixture of chloroform/methanol (85:15) as the eluant mixture

Sources & evidence

ORD record
ord-0ba2179fe9da450dbbba9609f375eac2
Source dataset
uspto-grants-1981_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04264599

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes