1-(Piperidin-4-yl)imidazolidin-2-one → 1-{1-[2-Hydroxy-3-(2-chloro-6-methyl-3-pyridyloxy)-propyl]-4-piperidyl}-imidazolidin-2-one

HRID 444449Notes

Reaction equation

HRID 444449 reaction equation
[Cl:1][C:2]1[C:7]([O:8][CH2:9][CH:10]2[O:12][CH2:11]2)=[CH:6][CH:5]=[C:4]([CH3:13])[N:3]=1.[NH:14]1[CH2:19][CH2:18][CH:17]([N:20]2[CH2:24][CH2:23][NH:22][C:21]2=[O:25])[CH2:16][CH2:15]1>C(O)(C)C>[OH:12][CH:10]([CH2:9][O:8][C:7]1[C:2]([Cl:1])=[N:3][C:4]([CH3:13])=[CH:5][CH:6]=1)[CH2:11][N:14]1[CH2:15][CH2:16][CH:17]([N:20]2[CH2:24][CH2:23][NH:22][C:21]2=[O:25])[CH2:18][CH2:19]1

Participants

4

Reactant 2

HCID 130317571-(Piperidin-4-yl)imidazolidin-2-oneHCID 234638122-Chloro-3-(2,3-epoxy-propoxy)-6-methylpyridine

Product 1

HCID 234637941-{1-[2-Hydroxy-3-(2-chloro-6-methyl-3-pyridyloxy)-propyl]-4-piperidyl}-imidazolidin-2-one

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

1.1 g of 2-chloro-3-(2,3-epoxy-propoxy)-6-methylpyridine and 0.76 g of 1-(4-piperidyl)-imidazolidin-2-one are refluxed in 40 ml of isopropanol for 1 hour. Evaporating off the solvent and recrystallising the residue from the isopropanol/ether yields 1-{1-[2-hydroxy-3-(2-chloro-6-methyl-3-pyridyloxy)-propyl]-4-piperidyl}-imidazolidin-2-one with a melting point of 175°-180°.

Workup

  1. customEvaporating off the solvent
  2. customrecrystallising the residue from the isopropanol/ether

Sources & evidence

ORD record
ord-85248c66ea0440f0970bd6e1c73d5b3a
Source dataset
uspto-grants-1981_04
Patent number
US04264599

Reaction notes

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