Benzyl Bromide → HCID 86614355, compound

HRID 2265157Notes

Reaction equation

HRID 2265157 reaction equation
C(=O)([O-])[O-].[K+].[K+].[CH2:7](Br)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[C:15]1([CH3:31])[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[CH:21]1[CH2:26][CH2:25][NH:24][CH2:23][CH:22]1[C:27]([O:29][CH3:30])=[O:28].C(=O)([O-])O.[Na+]>CN(C)C=O>[CH2:7]([N:24]1[CH2:25][CH2:26][CH:21]([C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=2[CH3:31])[CH:22]([C:27]([O:29][CH3:30])=[O:28])[CH2:23]1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

6

Reactant 4

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 516892Sodium BicarbonateHCID 86071099HCID 86071099, compound

Product 1

HCID 86614355HCID 86614355, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

540 mg of potassium carbonate and 0.25 mL of benzyl bromide were added to N,N-dimethylformamide (7 mL) solution of 453 mg of methyl (3RS,4SR)-4-o-tolyl-piperidine-3-carboxylate obtained in Production Example 31, and stirred at 70° C. for 1.5 hours. Then, this was restored to room temperature, aqueous saturated sodium hydrogencarbonate solution was added thereto and extracted with ether. The ether layer was washed with saturated saline water, and dried with anhydrous sodium sulfate, and the solvent was evaporated off under reduced pressure. The residue was separated and purified through silica gel column chroamtography (hexane/ethyl acetate=9/1) to obtain 463 mg of methyl (3RS,4SR)-1-benzyl-4-o-tolyl-piperidine-3-carboxylate. The compound was processed in the same manner as in Production Example 33-1 to obtain 360 mg of the entitled compound.

Workup

  1. customobtained in Production Example 31
  2. customthis was restored to room temperature
  3. extractionextracted with ether
  4. washThe ether layer was washed with saturated saline water
  5. dry with materialdried with anhydrous sodium sulfate
  6. customthe solvent was evaporated off under reduced pressure
  7. customThe residue was separated
  8. custompurified through silica gel column chroamtography (hexane/ethyl acetate=9/1)

Sources & evidence

ORD record
ord-50fb1f0765114e7ca6d5615c1a90e67b
Source dataset
uspto-grants-2010_12
Patent number
US07855294B2

Reaction notes

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