O-Xylene → 1-Benzyl-3-(3-methoxyphenyl)-1,2,5,6-tetrahydropyridine

HRID 851134Notes

Reaction equation

HRID 851134 reaction equation
Cl.[CH3:2][O:3][C:4]1[CH:5]=[C:6]([C:10]2(O)[CH2:15][CH2:14][CH2:13][N:12]([CH2:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[CH2:11]2)[CH:7]=[CH:8][CH:9]=1.C1(C)C(C)=CC=CC=1.O=P12OP3(OP(OP(O3)(O1)=O)(=O)O2)=O.C(N(CC)CC)C>O.C(OCC)(=O)C>[CH2:16]([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)[C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1

Participants

7

Reactant 4

HCID 7237O-XyleneHCID 8471TriethylamineHCID 14812Phosphorus oxide (P4O10)HCID 136950943-(3-Methoxyphenyl)-1-benzyl-piperidine-3-ol hydrochloride

Product 1

HCID 151054501-Benzyl-3-(3-methoxyphenyl)-1,2,5,6-tetrahydropyridineYield 72.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
140 °C

Procedure

A mixture of 3.25 g of the product of Step A and 65 ml of xylene was heated to 140° C. with stirring and after the addition of 2 g of phosphoric acid anhydride, the mixture was stirred at 140° C. for 2 hours and was then iced. Ice was then added to the mixture with caution and was diluted with water and ethyl acetate. The mixture was made alkaline by addition of triethylamine and was stirred until total dissolution occurred. The mixture was filtered and the decanted aqueous phase was extracted with ethyl acetate. The organic extract 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 a 9-1 cyclohexane-ethyl acetate mixture to obtain 1.97 g of 1-benzyl-3-(3-methoxyphenyl)-1,2,5,6-tetrahydropyridine.

Workup

  1. stirringthe mixture was stirred at 140° C. for 2 hours
  2. additionIce was then added to the mixture with caution
  3. stirringwas stirred until total dissolution
  4. filtrationThe mixture was filtered
  5. extractionthe decanted aqueous phase was extracted with ethyl acetate
  6. extractionThe organic extract
  7. washwas washed with aqueous saturated sodium chloride solution
  8. customdried
  9. customevaporated to dryness under reduced pressure
  10. customThe residue was chromatographed over silica gel
  11. washwas eluted with a 9-1 cyclohexane-ethyl acetate mixture

Sources & evidence

ORD record
ord-b96df321c70041cc925d100de1204379
Source dataset
uspto-grants-1983_05
Patent number
US04382942

Reaction notes

Loading…