2-Chloro-3-(2,3-epoxy-propoxy)-pyrazine → 1-{1-[2-Hydroxy-3-(3-chloro-pyrazin-2-yloxy)-propyl]-4-piperidinyl}-3-phenylimidazolidin-2-one

HRID 614370Notes

Reaction equation

HRID 614370 reaction equation
[Cl:1][C:2]1[C:7]([O:8][CH2:9][CH:10]2[O:12][CH2:11]2)=[N:6][CH:5]=[CH:4][N:3]=1.[NH:13]1[CH2:18][CH2:17][CH:16]([N:19]2[CH2:23][CH2:22][N:21]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[C:20]2=[O:30])[CH2:15][CH2:14]1>C(O)(C)C>[OH:12][CH:10]([CH2:9][O:8][C:7]1[C:2]([Cl:1])=[N:3][CH:4]=[CH:5][N:6]=1)[CH2:11][N:13]1[CH2:14][CH2:15][CH:16]([N:19]2[CH2:23][CH2:22][N:21]([C:24]3[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=3)[C:20]2=[O:30])[CH2:17][CH2:18]1

Participants

4

Reactant 2

HCID 128021292-Chloro-3-(2,3-epoxy-propoxy)-pyrazineHCID 205401631-Phenyl-3-(piperidin-4-yl)imidazolidin-2-one

Product 1

HCID 233473571-{1-[2-Hydroxy-3-(3-chloro-pyrazin-2-yloxy)-propyl]-4-piperidinyl}-3-phenylimidazolidin-2-one

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

7.27 g of 2-chloro-3-(2,3-epoxy-propoxy)-pyrazine and 7.35 g of 1-(4-piperidyl)-3-phenyl-2-imidazolidinone in 120 ml of isopropanol are stirred for 24 hours at approx. 20° C. The reaction mixture is then concentrated in a water jet vacuum. The residue crystallises from ether and yields 1-{1-[2-hydroxy-3-(3-chloro-pyrazin-2-yloxy)-propyl]-4-piperidinyl}-3-phenyl-imidazolidin-2-one with a melting point of 122°-124° C.

Workup

  1. concentrationThe reaction mixture is then concentrated in a water jet vacuum
  2. customThe residue crystallises from ether

Sources & evidence

ORD record
ord-40ebce1264c6476686f820f57cdc684e
Source dataset
uspto-grants-1979_03
Patent number
US04144344

Reaction notes

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