Potassium Iodide → N-phenethyl-4-(2-bromo-5-methoxy-benzyl)piperidine

HRID 1006058Notes

Reaction equation

HRID 1006058 reaction equation
Cl.[Br:2][C:3]1[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[CH:12][C:4]=1[CH2:5][CH:6]1[CH2:11][CH2:10][NH:9][CH2:8][CH2:7]1.[OH-].[Na+].[CH2:20](Br)[CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.C(=O)([O-])[O-].[K+].[K+].[I-].[K+]>C(#N)C>[CH2:20]([N:9]1[CH2:8][CH2:7][CH:6]([CH2:5][C:4]2[CH:12]=[C:13]([O:16][CH3:17])[CH:14]=[CH:15][C:3]=2[Br:2])[CH2:11][CH2:10]1)[CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

7

Reactant 5

HCID 4875Potassium IodideHCID 7666Phenethyl bromideHCID 11430Potassium CarbonateHCID 14798Sodium HydroxideHCID 226753344-(2-Bromo-5-methoxybenzyl)piperidine hydrochloride

Product 1

HCID 12968865N-phenethyl-4-(2-bromo-5-methoxy-benzyl)piperidineYield 58.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

4-(2-Bromo-5-methoxybenzyl)piperidine hydrochloride (192 mg, 0.60 mmol) was neutralized with a 1N-aqueous sodium hydroxide solution, followed by extraction with diethyl ether, whereby a corresponding free compound was obtained. A mixture of the free compound, phenethyl bromide (110 mg, 0.594 mmol), potassium carbonate (250 mg, 1.81 mmol), potassium iodide (10.3 mg, 0.062 mmol) and acetonitrile (3.6 mL) was heated under reflux under nitrogen for 8 hours. After the inorganic matters were filtered off, the filtrate was concentrated under reduced pressure and the concentration residue was purified by a flash silica gel column chromatography (hexane/ethyl acetate/triethylamine=5/15/0 to 5/15/1) to obtain N-phenethyl-4-(2-bromo-5-methoxy-benzyl)piperidine (134 mg, 58%) as an oil.

Workup

  1. extractionfollowed by extraction with diethyl ether, whereby a corresponding free compound
  2. customwas obtained
  3. temperaturewas heated
  4. temperatureunder reflux under nitrogen for 8 hours
  5. filtrationAfter the inorganic matters were filtered off
  6. concentrationthe filtrate was concentrated under reduced pressure
  7. customthe concentration residue was purified by a flash silica gel column chromatography (hexane/ethyl acetate/triethylamine=5/15/0 to 5/15/1)

Sources & evidence

ORD record
ord-eaef8a639cbc48398ec393a6080f3b49
Source dataset
uspto-grants-2004_09
Patent number
US06787560B2

Reaction notes

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