Phenethyl bromide → 3-(3,4-Dimethoxyphenyl)-1-(2-phenylethyl)piperidine

HRID 616035Notes

Reaction equation

HRID 616035 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:11]2[CH2:16][CH2:15][CH2:14][NH:13][CH2:12]2)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].[CH2:17](Br)[CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>C(Cl)(Cl)Cl.[Ag]=O>[C:19]1([CH2:18][CH2:17][N:13]2[CH2:14][CH2:15][CH2:16][CH:11]([C:5]3[CH:6]=[CH:7][C:8]([O:9][CH3:10])=[C:3]([O:2][CH3:1])[CH:4]=3)[CH2:12]2)[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

5

Reactant 2

HCID 7666Phenethyl bromide2×HCID 129379213-(3,4-Dimethoxyphenyl)piperidine

Product 1

HCID 203708433-(3,4-Dimethoxyphenyl)-1-(2-phenylethyl)piperidine

Reagents, catalysts & solvents 2

HCID 92152Silver(II) oxideCatalyst2×HCID 6212ChloroformSolvent

Procedure

500 mg of silver oxide were added to a mixture of 1 g of 3-(3',4'-dimethoxyphenyl)-piperidine in 5 ml of chloroform and then 0.7 ml of phenethyl bromide was added thereto dropwise. The mixture was stirred for 6 hours at room temperature and then 250 mg of silver oxide and 0.35 ml of phenethyl bromide were added thereto. The mixture was stirred at room temperature for 16 hours and was filtered to remove insolubles. The filtrate was evaporated to dryness under reduced pressure and the residue was chromatographed over silica gel. Elution with a 6-3-1 cyclohexane-chloroform-triethylamine mixture yielded 1.045 g of amorphous N-(β-phenylethyl)-3-(3',4'-dimethoxyphenyl)-piperidine.

Workup

  1. stirringThe mixture was stirred at room temperature for 16 hours
  2. filtrationwas filtered
  3. customto remove insolubles
  4. customThe filtrate was evaporated to dryness under reduced pressure
  5. customthe residue was chromatographed over silica gel
  6. washElution with a 6-3-1 cyclohexane-chloroform-triethylamine mixture

Sources & evidence

ORD record
ord-2a0a806888fa40129e0e8fbc42da57b0
Source dataset
uspto-grants-1978_02
Patent number
US04072685

Reaction notes

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