Potassium Carbonate → HCID 11978980, compound

HRID 657631Notes

Reaction equation

HRID 657631 reaction equation
C(=O)([O-])[O-].[K+].[K+].Br[C:8]1[CH:23]=[CH:22][C:11]([O:12][CH2:13][CH2:14][CH2:15][N:16]2[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]2)=[CH:10][CH:9]=1.[CH3:24][C:25]1[CH:30]=[CH:29][C:28](B(O)O)=[CH:27][CH:26]=1>C1(C)C=CC=CC=1.C(OCC)(=O)C>[CH3:24][C:25]1[CH:30]=[CH:29][C:28]([C:8]2[CH:23]=[CH:22][C:11]([O:12][CH2:13][CH2:14][CH2:15][N:16]3[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]3)=[CH:10][CH:9]=2)=[CH:27][CH:26]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 79799Tolylboronic acidHCID 2058924HCID 2058924, compound

Product 1

HCID 11978980HCID 11978980, compoundYield 27%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A suspension of potassium carbonate (290 mg) and palladium tetrakistriphenylphosphine (49 mg) in a solution of 1-[3-(4-bromophenoxy)-propyl]piperidine (250 mg) and 4-methylbenzeneboronic acid (228 mg) in toluene (5 mL) is heated overnight at a temperature close to 100° C. The mixture is diluted with ethyl acetate (200 mL) washed with a saturated aqueous sodium bicarbonate solution (3 mL), dried over magnesium sulphate, concentrated under reduced pressure and purified by chromatography over silica gel with dichloromethane then dichloromethane/methanol/ammonia 99/1/0.5. Fractions containing the expected product are pooled, concentrated under reduced pressure and salted with oxalic acid to give 70 mg of 1-{3-[(4′-methylbiphenyl-4-yl)oxy]propyl}piperidine, oxalate as a white solid melting at 195° C.

Workup

  1. temperatureis heated overnight at a temperature
  2. customclose to 100° C
  3. washwashed with a saturated aqueous sodium bicarbonate solution (3 mL)
  4. dry with materialdried over magnesium sulphate
  5. concentrationconcentrated under reduced pressure
  6. custompurified by chromatography over silica gel with dichloromethane
  7. additionFractions containing the expected product
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-5295045bc7924fc18c70f06cb3a9aa60
Source dataset
uspto-grants-2011_12
Patent number
US08076329B2

Reaction notes

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