HCID 20266415, compound → HCID 20266422, compound

HRID 1719714Notes

Reaction equation

HRID 1719714 reaction equation
[Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=CC=1.[CH3:12][O:13][C:14]1[CH:15]=[C:16]2[C:21](=[CH:22][C:23]=1[O:24][CH3:25])[N:20]=[CH:19][N:18]=[C:17]2[N:26]1[CH2:31][CH2:30][CH:29]([CH:32]([OH:34])[CH3:33])[CH2:28][CH2:27]1>ClCCl>[CH3:12][O:13][C:14]1[CH:15]=[C:16]2[C:21](=[CH:22][C:23]=1[O:24][CH3:25])[N:20]=[CH:19][N:18]=[C:17]2[N:26]1[CH2:31][CH2:30][CH:29]([C:32](=[O:34])[CH3:33])[CH2:28][CH2:27]1

Participants

4

Reactant 2

HCID 20266415HCID 20266415, compoundHCID 178418287HCID 178418287, compound

Product 1

HCID 20266422HCID 20266422, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Pyridinium chlorochromate (6.2 g) was added at room temperature to a stirred solution of 6,7-dimethoxy-4-[4-(1-hydroxyethyl)piperid-1-yl]quinazoline (7.60 g) in dichloromethane (150 cm3) and the mixture was stirred for 24 hours. The mixture was filtered through "Avicel" (Trademark) and the solution was washed with 2M sodium hydroxide (3×50 cm3). The dried (MgSO4) organic phase was evaporated and the residue chromatographed on silica ("Merck" 60.9385) eluting with chloroform to give a solid which was recrystallized from ethyl acetate to afford 6,7-dimethoxy-4-[4-(1-oxoethyl)piperid-1-yl]quinazoline, m.p. 116°-117° (3.05 g).

Workup

  1. filtrationThe mixture was filtered through "Avicel" (Trademark)
  2. washthe solution was washed with 2M sodium hydroxide (3×50 cm3)
  3. dry with materialThe dried (MgSO4) organic phase
  4. customwas evaporated
  5. customthe residue chromatographed on silica ("Merck" 60.9385)
  6. washeluting with chloroform
  7. customto give a solid which
  8. customwas recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-fe846538a808467483d4cf60737b69a0
Source dataset
uspto-grants-1985_09
Patent number
US04542132

Reaction notes

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