HCID 23499365, compound → HCID 23499296, compound

HRID 1836352Notes

Reaction equation

HRID 1836352 reaction equation
C[O:2][C:3]1[CH:4]=[C:5]([CH:15]=[CH:16][CH:17]=1)[C:6]([CH:8]1[CH2:13][CH2:12][N:11]([CH3:14])[CH2:10][CH2:9]1)=[O:7]>Br>[OH:2][C:3]1[CH:4]=[C:5]([CH:15]=[CH:16][CH:17]=1)[C:6]([CH:8]1[CH2:9][CH2:10][N:11]([CH3:14])[CH2:12][CH2:13]1)=[O:7]

Participants

3

Reactant 1

HCID 23499365HCID 23499365, compound

Product 1

HCID 23499296HCID 23499296, compoundYield 99.5%

Reagents, catalysts & solvents 1

HCID 260Hydrogen BromideSolvent

Procedure

A solution of 4-[3-methoxybenzoyl]-1-methylpiperidine (260 mg, 1.1 mmol) in 48% hydrobromic acid (10 mL) was refluxed for 1 h. The reaction mixture was concentrated under reduced pressure to a brown oil. The oil was dissolved in water, basified to pH 9 with ammonium hydroxide, and extracted with methylene chloride. Sodium chloride was added to the aqueous phase and extracted with chloroform/isopropanol (3:1). The organic extracts were combined, dried over sodium sulfate, and concentrated in vacuo to give 240 mg of a tan solid. Purification by radial chromatography (silica gel, 2000 micron rotor, methylene chloride:methanol:ammonium hydroxide, 100:10:1) gave 214 mg (88%) of a tan crystalline solid. Mp 161-4° C. MS(m/e): 220(M+1).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure to a brown oil
  2. dissolutionThe oil was dissolved in water
  3. extractionextracted with methylene chloride
  4. additionSodium chloride was added to the aqueous phase
  5. extractionextracted with chloroform/isopropanol (3:1)
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-de3635be709d4645a38c0e161c0b38a5
Source dataset
uspto-grants-2004_08
Patent number
US06777428B1

Reaction notes

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