Phenethyl bromide → 5-(3-Methoxyphenyl)-1-(2-phenylethyl)-1,2,3,6-tetrahydropyridine

HRID 851139Notes

Reaction equation

HRID 851139 reaction equation
Cl.[CH3:2][O:3][C:4]1[CH:5]=[C:6]([C:10]2[CH2:11][NH:12][CH2:13][CH2:14][CH:15]=2)[CH:7]=[CH:8][CH:9]=1.C(=O)([O-])[O-].[Na+].[Na+].[CH2:22](Br)[CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>CC(C)=O>[CH3:2][O:3][C:4]1[CH:5]=[C:6]([C:10]2[CH2:11][N:12]([CH2:22][CH2:23][C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[CH2:13][CH2:14][CH:15]=2)[CH:7]=[CH:8][CH:9]=1

Participants

5

Reactant 3

HCID 7666Phenethyl bromideHCID 10340Sodium CarbonateHCID 130667493-(3-Methoxyphenyl)-1,2,5,6-tetrahydropyridine hydrochloride

Product 1

HCID 132342035-(3-Methoxyphenyl)-1-(2-phenylethyl)-1,2,3,6-tetrahydropyridine

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 5 g of 3-(3-methoxyphenyl)-1,2,5,6-tetrahydropyridine hydrochloride, 100 ml of acetone, 7 g of sodium carbonate and 3.5 ml of phenethyl bromide was refluxed for 16 hours and was filtered. The filtrate was evaporated to dryness and the residue was chromatographed over silica gel. The elution with a 7-3 cyclohexane-ethyl acetate mixture yielded 6.2 g of 3-(3-methoxyphenyl)-1-phenethyl-1,2,5,6-tetrahydropyridine.

Workup

  1. temperaturewas refluxed for 16 hours
  2. filtrationwas filtered
  3. customThe filtrate was evaporated to dryness
  4. customthe residue was chromatographed over silica gel
  5. washThe elution with a 7-3 cyclohexane-ethyl acetate mixture

Sources & evidence

ORD record
ord-bffbb67ecc56421c96d29c5cb46e51be
Source dataset
uspto-grants-1983_05
Patent number
US04382942

Reaction notes

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