Dimethylformamide → 1-Ethyl-5-(3-methoxyphenyl)-1,2,3,6-tetrahydropyridine

HRID 851141Notes

Reaction equation

HRID 851141 reaction equation
C(=O)([O-])[O-].[Na+].[Na+].[CH2:7](I)[CH3:8].Cl.[CH3:11][O:12][C:13]1[CH:14]=[C:15]([C:19]2[CH2:20][NH:21][CH2:22][CH2:23][CH:24]=2)[CH:16]=[CH:17][CH:18]=1.CN(C)C=O>O>[CH3:11][O:12][C:13]1[CH:14]=[C:15]([C:19]2[CH2:20][N:21]([CH2:7][CH3:8])[CH2:22][CH2:23][CH:24]=2)[CH:16]=[CH:17][CH:18]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 6340IodoethaneHCID 10340Sodium CarbonateHCID 130667493-(3-Methoxyphenyl)-1,2,5,6-tetrahydropyridine hydrochloride

Product 1

HCID 205026301-Ethyl-5-(3-methoxyphenyl)-1,2,3,6-tetrahydropyridine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

9.8 g of sodium carbonate and 2.6 ml of ethyl iodide were added to a suspension of 7 g of 3-(3-methoxyphenyl)-1,2,5,6-tetrahydropyridine hydrochloride and 70 ml of dimethylformamide and the mixture was stirred for 16 hours and was diluted with water. The mixture was extracted with ethyl acetate and the organic extract was washed with water, 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 to obtain 5.3 g of 3-(3-methoxyphenyl)-1-ethyl-1,2,5,6-tetrahydropyridine.

Workup

  1. extractionThe mixture was extracted with ethyl acetate
  2. extractionthe organic extract
  3. washwas washed with water
  4. customdried
  5. customevaporated to dryness under reduced pressure
  6. customThe residue was chromatographed over silica gel
  7. washwas eluted with an 8-1-1 cyclohexane-chloroform-triethylamine mixture

Sources & evidence

ORD record
ord-4076ac29e63249169542e3ef4b07f737
Source dataset
uspto-grants-1983_05
Patent number
US04382942

Reaction notes

Loading…