HCID 67000209, compound → HCID 59318289, compound

HRID 1623221Notes

Reaction equation

HRID 1623221 reaction equation
Cl.[Br:2][C:3]1[CH:15]=[CH:14][C:6]([CH2:7][CH:8]2[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]2)=[CH:5][C:4]=1[O:16][CH2:17][CH2:18][O:19][CH3:20]>C(=O)([O-])[O-].[K+].[K+]>[Br:2][C:3]1[CH:15]=[CH:14][C:6]([CH2:7][CH:8]2[CH2:9][CH2:10][NH:11][CH2:12][CH2:13]2)=[CH:5][C:4]=1[O:16][CH2:17][CH2:18][O:19][CH3:20]

Participants

3

Reactant 1

HCID 67000209HCID 67000209, compound

Product 1

HCID 59318289HCID 59318289, compoundYield 102.5%

Reagents, catalysts & solvents 1

HCID 11430Potassium CarbonateSolvent

Procedure

4-[4-Bromo-3-(2-methoxyethoxy)benzyl]piperidine hydrochloride (RE1) (52.0 g, 143 mmol) was added to a 5% aqueous potassium carbonate solution (350 mL), followed by extraction with toluene (700 mL×3). Combined organic layers were dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure to obtain 4-[4-bromo-3-(2-methoxyethoxy)benzyl]piperidine (48.1 g). Next, a solution of 4-[4-bromo-3-(2-methoxyethoxy)benzyl]piperidine (2.00 g, 6.1 mmol), 2-(4-oxo-3,4-dihydro-2H-chromen-6-yl)ethyl 4-methylbenzenesulfonate (RE6) (2.01 g, 5.8 mmol) and potassium carbonate (1.66 g, 12 mmol) in acetonitrile (20 mL) was stirred at 70 to 80° C. for 7 hours. After cooling to room temperature, water (100 mL) was added thereto, followed by extraction with chloroform. The chloroform layer was dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure, and then, the obtained concentrated residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=1:1→chloroform:methanol=20:1) to obtain the title compound (5-1-1) (3.07 g, quantitative).

Workup

  1. extractionfollowed by extraction with toluene (700 mL×3)
  2. dry with materialCombined organic layers were dried over anhydrous sodium sulfate
  3. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-7028e70c994b487fb5c9d345c99b70c4
Source dataset
uspto-grants-2014_07
Patent number
US08778970B2

Reaction notes

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