Allyl bromide → 5-(3-Methoxyphenyl)-1-(prop-2-en-1-yl)-1,2,3,6-tetrahydropyridine

HRID 851146Notes

Reaction equation

HRID 851146 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)[CH:23]=[CH2:24]>CN(C)C=O>[CH2:24]([N:12]1[CH2:13][CH2:14][CH:15]=[C:10]([C:6]2[CH:7]=[CH:8][CH:9]=[C:4]([O:3][CH3:2])[CH:5]=2)[CH2:11]1)[CH:23]=[CH2:22]

Participants

5

Reactant 3

HCID 7841Allyl bromideHCID 10340Sodium CarbonateHCID 130667493-(3-Methoxyphenyl)-1,2,5,6-tetrahydropyridine hydrochloride

Product 1

HCID 205026425-(3-Methoxyphenyl)-1-(prop-2-en-1-yl)-1,2,3,6-tetrahydropyridineYield 83%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 7 g of 3-(3-methoxyphenyl)-1,2,5,6-tetrahydropyridine hydrochloride, 100 ml of dimethylformamide, 9.8 g of sodium carbonate and 3.75 g of allyl bromide was stirred for 6 hours and was then filtered. The filtrate was evaporated to dryness and the residue was chromatographed over silica gel. Elution with a 7-3 benzene-ethyl acetate mixture yielded 5.9 g of 1-allyl-3-(3-methoxyphenyl)-1,2,5,6-tetrahydropyridine.

Workup

  1. filtrationwas then filtered
  2. customThe filtrate was evaporated to dryness
  3. customthe residue was chromatographed over silica gel
  4. washElution with a 7-3 benzene-ethyl acetate mixture

Sources & evidence

ORD record
ord-f85269c6a9324960aa5b173cf6107487
Source dataset
uspto-grants-1983_05
Patent number
US04382942

Reaction notes

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