Sodium Methoxide → 1-{1-[2-Hydroxy-3-(3-methoxy-pyrazin-2-yloxy)-propyl]-4-piperidinyl}-3-phenyl-imidazolidin-2-one

HRID 1855998Notes

Reaction equation

HRID 1855998 reaction equation
[OH:1][CH:2]([CH2:22][O:23][C:24]1[C:29](Cl)=[N:28][CH:27]=[CH:26][N:25]=1)[CH2:3][N:4]1[CH2:9][CH2:8][CH:7]([N:10]2[CH2:14][CH2:13][N:12]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[C:11]2=[O:21])[CH2:6][CH2:5]1.[CH3:31][O-:32].[Na+]>CO>[OH:1][CH:2]([CH2:22][O:23][C:24]1[C:29]([O:32][CH3:31])=[N:28][CH:27]=[CH:26][N:25]=1)[CH2:3][N:4]1[CH2:9][CH2:8][CH:7]([N:10]2[CH2:14][CH2:13][N:12]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[C:11]2=[O:21])[CH2:6][CH2:5]1

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 233473571-{1-[2-Hydroxy-3-(3-chloro-pyrazin-2-yloxy)-propyl]-4-piperidinyl}-3-phenylimidazolidin-2-one

Product 1

HCID 233473411-{1-[2-Hydroxy-3-(3-methoxy-pyrazin-2-yloxy)-propyl]-4-piperidinyl}-3-phenyl-imidazolidin-2-one

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

With stirring, 10.1 g of 1-{1-[2-hydroxy-3-(3-chloropyrazin-2-yloxy)-propyl]-4-piperidinyl}-3-phenyl-imidazolidin-2-one (see Example 6) and 1.41 g of sodium methylate in 110 ml of methanol are refluxed for 10 hours. The reaction mixture is concentrated in a water jet vacuum. The residue is dissolved in ethyl acetate and extracted with 2 N hydrochloric acid. The combined hydrochloric acid extracts are made alkaline with conc. ammonia and extracted with methylene chloride. The combined methylene chloride extracts are washed with water, dried over sodium sulphate and concentrated in a water jet vacuum. The residue crystallises from methylene chloride-ether to yield 1-{1-[2-hydroxy-3-(3-methoxy-pyrazin-2-yloxy)-propyl]-4-piperidinyl}-3-phenyl-imidazolidin-2-one with a melting point of 128°-129° C.

Workup

  1. concentrationThe reaction mixture is concentrated in a water jet vacuum
  2. dissolutionThe residue is dissolved in ethyl acetate
  3. extractionextracted with 2 N hydrochloric acid
  4. extractionextracted with methylene chloride
  5. washThe combined methylene chloride extracts are washed with water
  6. dry with materialdried over sodium sulphate
  7. concentrationconcentrated in a water jet vacuum
  8. customThe residue crystallises from methylene chloride-ether

Sources & evidence

ORD record
ord-9e7e5ad46d814b71893ccb65a7adddff
Source dataset
uspto-grants-1980_08
Patent number
US04217350

Reaction notes

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