Hydrochloric Acid → 3-(2-Hydroxyethyl)-1-(4-piperidyl)-imidazolidin-2-one
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]Participants
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
- customis hydrogenated at room temperature
- filtrationThe catalyst is then filtered off
- customthe filtrate is evaporated under reduced pressure
- customThe reaction product is chromatographed on 2 kg of basic aluminium oxide using
- additiona mixture of chloroform/methanol (85:15) as the eluant mixture
Sources & evidence
- ORD record
- ord-0ba2179fe9da450dbbba9609f375eac2
- Source dataset
- uspto-grants-1981_04
- Patent number
- US04264599
Reaction notes
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