HCID 68524346, compound → HCID 24898775, compound

HRID 1515225Notes

Reaction equation

HRID 1515225 reaction equation
[Br:1][C:2]1[CH:24]=[CH:23][C:5]2[O:6][CH2:7][C:8]3[CH:22]=[CH:21][CH:20]=[CH:19][C:9]=3[C:10]([CH:12]3[CH2:17][CH2:16][N:15]([CH3:18])[CH2:14][CH2:13]3)(O)[C:4]=2[CH:3]=1>C(O)(C(F)(F)F)=O>[Br:1][C:2]1[CH:24]=[CH:23][C:5]2[O:6][CH2:7][C:8]3[CH:22]=[CH:21][CH:20]=[CH:19][C:9]=3[C:10](=[C:12]3[CH2:17][CH2:16][N:15]([CH3:18])[CH2:14][CH2:13]3)[C:4]=2[CH:3]=1

Participants

3

Reactant 1

HCID 68524346HCID 68524346, compound

Product 1

HCID 24898775HCID 24898775, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

A TFA (150 mL) solution of 2-bromo-11-(1-methylpiperidin-4-yl)-6,11-dihydrodibenz[b,e]oxepin-11-ol (21.7 g, 56.0 mmol) was stirred overnight at room temperature. The solvent was distilled off under a reduced pressure, a 10% aqueous potassium carbonate solution was then added to the residue to neutralize, and the product was extracted with ethyl acetate. The extract was dried over anhydrous sodium sulfate, the solvent was then distilled off under a reduced pressure, and the reside was purified by column chromatography (chloroform-methanol=9:1), to give 15.1 g (73%) of the captioned compound in the form of crystals.

Workup

  1. distillationThe solvent was distilled off under a reduced pressure
  2. additiona 10% aqueous potassium carbonate solution was then added to the residue
  3. extractionthe product was extracted with ethyl acetate
  4. dry with materialThe extract was dried over anhydrous sodium sulfate
  5. distillationthe solvent was then distilled off under a reduced pressure
  6. customthe reside was purified by column chromatography (chloroform-methanol=9:1)

Sources & evidence

ORD record
ord-4df1e7eab24b4183b86703baf4bd1801
Source dataset
uspto-grants-2012_07
Patent number
US08222419B2

Reaction notes

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