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

HRID 614373Notes

Reaction equation

HRID 614373 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 2N 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 2N 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-47634168bf0346a3b57f530a43aa9672
Source dataset
uspto-grants-1979_03
Patent number
US04144344

Reaction notes

Loading…