Phenacyl bromide → 1-Phenyl-2-[3-(3-methoxyphenyl)-1,2,5,6-tetrahydropyridin-1-yl]-ethanone

HRID 851144Notes

Reaction equation

HRID 851144 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)[C:23]([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)=[O:24]>CC(C)=O>[C:25]1([C:23](=[O:24])[CH2:22][N:12]2[CH2:13][CH2:14][CH:15]=[C:10]([C:6]3[CH:7]=[CH:8][CH:9]=[C:4]([O:3][CH3:2])[CH:5]=3)[CH2:11]2)[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

Participants

5

Reactant 3

HCID 6259Phenacyl bromideHCID 10340Sodium CarbonateHCID 130667493-(3-Methoxyphenyl)-1,2,5,6-tetrahydropyridine hydrochloride

Product 1

HCID 205026351-Phenyl-2-[3-(3-methoxyphenyl)-1,2,5,6-tetrahydropyridin-1-yl]-ethanoneYield 102.8%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 10 g of 3-(3-methoxyphenyl)-1,2,5,6-tetrahydropyridine hydrochloride, 200 ml of acetone, 14 g of sodium carbonate and 9.3 g of phenacyl bromide were refluxed for 3 hours and was filtered. The filtrate was evaporated to dryness to obtain 14 g of 1-phenyl-2-[3-(3-methoxyphenyl)-1,2,5,6-tetrahydropyridin-1-yl]-ethanone.

Workup

  1. temperaturewere refluxed for 3 hours
  2. filtrationwas filtered
  3. customThe filtrate was evaporated to dryness

Sources & evidence

ORD record
ord-bc57e7602f544336bcb77a7bb923f307
Source dataset
uspto-grants-1983_05
Patent number
US04382942

Reaction notes

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