Water → 3-(3-Methoxyphenyl)-1-propyl-1,2,5,6-tetrahydropyridine

HRID 851137Notes

Reaction equation

HRID 851137 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](I)[CH2:23][CH3:24].O>CN(C)C=O>[CH3:2][O:3][C:4]1[CH:5]=[C:6]([C:10]2[CH2:11][N:12]([CH2:22][CH2:23][CH3:24])[CH2:13][CH2:14][CH:15]=2)[CH:7]=[CH:8][CH:9]=1

Participants

6

Reactant 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 336431-IodopropaneHCID 130667493-(3-Methoxyphenyl)-1,2,5,6-tetrahydropyridine hydrochloride

Product 1

HCID 136951003-(3-Methoxyphenyl)-1-propyl-1,2,5,6-tetrahydropyridine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of a solution of 5 g of the product of Step D of Example 3 in 50 ml of dimethylformamide, 7 g of sodium carbonate and 2.3 ml of n-propyl iodide was stirred for 16 hours under an inert atmosphere and was then poured into 250 ml of iced water. The mixture was extracted with ethyl acetate and the organic phase was washed with aqueous saturated sodium chloride solution, dried and evaporated to dryness under reduced pressure. The residue was chromatographed over silica gel and was eluted with an 8-1-1 cyclohexane-chloroform-triethylamine mixture. The eluate was distilled to dryness under reduced pressure to obtain 4.84 g of 3-(3-methoxyphenyl)-1-propyl-1,2,5,6-tetrahydropyridine.

Workup

  1. extractionThe mixture was extracted with ethyl acetate
  2. washthe organic phase was washed with aqueous saturated sodium chloride solution
  3. customdried
  4. customevaporated to dryness under reduced pressure
  5. customThe residue was chromatographed over silica gel
  6. washwas eluted with an 8-1-1 cyclohexane-chloroform-triethylamine mixture
  7. distillationThe eluate was distilled to dryness under reduced pressure

Sources & evidence

ORD record
ord-643b0c9f2daa469188214572c6198452
Source dataset
uspto-grants-1983_05
Patent number
US04382942

Reaction notes

Loading…