Ethanol → HCID 178518696, compound

HRID 1382773Notes

Reaction equation

HRID 1382773 reaction equation
[N:1]1([CH2:7][C:8]2[CH:9]=[C:10]([CH:31]=[CH:32][CH:33]=2)[O:11][CH2:12][CH2:13][CH2:14][C:15]2[NH:20][C:19](=[O:21])[C:18]([CH2:22][C:23]3[CH:28]=[CH:27][N:26]=[C:25]([O:29]C)[CH:24]=3)=[CH:17][N:16]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C(O)C>Cl>[N:1]1([CH2:7][C:8]2[CH:9]=[C:10]([CH:31]=[CH:32][CH:33]=2)[O:11][CH2:12][CH2:13][CH2:14][C:15]2[NH:20][C:19](=[O:21])[C:18]([CH2:22][C:23]3[CH:28]=[CH:27][N:26]=[C:25]([OH:29])[CH:24]=3)=[CH:17][N:16]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 702EthanolHCID 21273300HCID 21273300, compound

Product 1

HCID 178518696HCID 178518696, compoundYield 82.2%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

2-[[3-[3-(1-Piperidinylmethyl)phenoxy]propyl]]-5-(2-methoxy-4-pyridylmethyl)-4-pyrimidone (0.49 g) was dissolved in ethanolic hydrogen chloride (5 ml) and ethanol (25 ml) and the solution refluxed for 45 hours. Solvent was evaporated off under reduced pressure and the residue dissolved in water (25 ml). The solution was adjusted to pH 11 with potassium carbonate solution, whereupon an oily solid precipitated This was extracted with chloroform (3×20 ml) and the combined extracts dried (MgSO4) and chloroform evaporated in vacuo. The residue was recrystallised from isopropanol-ether to give 2-[[3-[3-(1-piperidinylmethyl)phenoxy]propyl]]-5-(2-hydroxy-4-pyridylmethyl)-4-pyrimidone as a white solid (0.39 g), m.p. 167°-9° C.

Workup

  1. customSolvent was evaporated off under reduced pressure
  2. dissolutionthe residue dissolved in water (25 ml)
  3. customprecipitated
  4. extractionThis was extracted with chloroform (3×20 ml)
  5. dry with materialthe combined extracts dried (MgSO4) and chloroform
  6. customevaporated in vacuo
  7. customThe residue was recrystallised from isopropanol-ether

Sources & evidence

ORD record
ord-4caf4cb6ddf24a0e87416086ad6924e8
Source dataset
uspto-grants-1989_02
Patent number
US04808589

Reaction notes

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