Sodium Carbonate → 3-[4-(3-Methoxyphenyl)-2,6-dimethylphenoxymethyl]-1-methylpiperidine

HRID 1872680Notes

Reaction equation

HRID 1872680 reaction equation
Br[C:2]1[CH:16]=[C:15]([CH3:17])[C:5]([O:6][CH2:7][CH:8]2[CH2:13][CH2:12][CH2:11][N:10]([CH3:14])[CH2:9]2)=[C:4]([CH3:18])[CH:3]=1.[CH3:19][O:20][C:21]1[CH:22]=[C:23](B(O)O)[CH:24]=[CH:25][CH:26]=1.C(=O)([O-])[O-].[Na+].[Na+]>C1(C)C=CC=CC=1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:19][O:20][C:21]1[CH:26]=[C:25]([C:2]2[CH:16]=[C:15]([CH3:17])[C:5]([O:6][CH2:7][CH:8]3[CH2:13][CH2:12][CH2:11][N:10]([CH3:14])[CH2:9]3)=[C:4]([CH3:18])[CH:3]=2)[CH:24]=[CH:23][CH:22]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 2734370(3-Methoxyphenyl)boronic acidHCID 99486563-(4-Bromo-2,6-dimethylphenoxymethyl)-1-methylpiperidine

Product 1

HCID 211841583-[4-(3-Methoxyphenyl)-2,6-dimethylphenoxymethyl]-1-methylpiperidine

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 3-(4-bromo-2,6-dimethylphenoxymethyl)-1-methylpiperidine (531 mg, 1.70 mmol) in toluene (10 mL) was added 3-methoxyphenylboronic acid (319 mg, 2.10 mmol), tetrakis(triphenylphosphine)palladium(0) (58 mg, 0.05 mmol), and 2M sodium carbonate (1.7 mL, 3.4 mmol). The mixture was stirred at 100° C. overnight and cooled to room temperature. The solution was partitioned between water and ethyl acetate. The organic layer was washed twice with water, brine, and dried. The solvent was removed and the residue purified on silica gel, eluting with 5% methanol in dichloromethane containing 0.25% ammonium hydroxide, to give 3-[4-(3-methoxyphenyl)-2,6-dimethylphenoxymethyl]-1-methylpiperidine.

Workup

  1. temperaturecooled to room temperature
  2. customThe solution was partitioned between water and ethyl acetate
  3. washThe organic layer was washed twice with water, brine
  4. customdried
  5. customThe solvent was removed
  6. customthe residue purified on silica gel
  7. washeluting with 5% methanol in dichloromethane containing 0.25% ammonium hydroxide

Sources & evidence

ORD record
ord-d3e0d0ca4b2c4794ac1b1170acd41ae3
Source dataset
uspto-grants-2000_08
Patent number
US06110937

Reaction notes

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