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

HRID 851143Notes

Reaction equation

HRID 851143 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.CN(C)C=O.C(=O)([O-])[O-].[Na+].[Na+].Cl[CH2:28][CH:29]1[CH2:31][CH2:30]1>O>[CH:29]1([CH2:28][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)[CH2:31][CH2:30]1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 10340Sodium CarbonateHCID 80013(Chloromethyl)cyclopropaneHCID 130667493-(3-Methoxyphenyl)-1,2,5,6-tetrahydropyridine hydrochloride

Product 1

HCID 205026391-(Cyclopropylmethyl)-5-(3-methoxyphenyl)-1,2,3,6-tetrahydropyridine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
75 °C

Procedure

A mixture of 10 g of 3-(3-methoxyphenyl)-1,2,5,6-tetrahydropyridine hydrochloride, 100 ml of dimethylformamide, 14 g of sodium carbonate and 4.4 ml of chloromethyl cyclopropane was heated at 75° C. for 24 hours and was then cooled and diluted with water. The mixture was extracted with ethyl acetate and the organic phase 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 9.25 g of 1-cyclopropylmethyl-3-(3-methoxyphenyl)-1,2,5,6-tetrahydropyridine.

Workup

  1. temperaturewas then cooled
  2. extractionThe mixture was extracted with ethyl acetate
  3. washthe organic phase was 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-5f217856cc504a97a0c0949a12d5c889
Source dataset
uspto-grants-1983_05
Patent number
US04382942

Reaction notes

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