Piperidine → 1-Methyl-4-(3-methoxyphenyl)-1,2,3,6-tetrahydropyridine

HRID 1277523Notes

Reaction equation

HRID 1277523 reaction equation
O=P12OP3(OP(OP(O3)(O1)=O)(=O)O2)=O.[CH3:15][N:16]1[CH2:21][CH2:20][C:19](O)([C:22]2[CH:27]=[CH:26][CH:25]=[C:24]([OH:28])[CH:23]=2)[CH2:18][CH2:17]1.N1CCCC[CH2:31]1.[OH-].[NH4+]>CS(O)(=O)=O>[CH3:15][N:16]1[CH2:21][CH2:20][C:19]([C:22]2[CH:27]=[CH:26][CH:25]=[C:24]([O:28][CH3:31])[CH:23]=2)=[CH:18][CH2:17]1

Participants

6

Reactant 4

HCID 8082PiperidineHCID 14812Phosphorus oxide (P4O10)HCID 14923Ammonium HydroxideHCID 205344404-(3-Hydroxyphenyl)-1-methyl-4-piperidinol

Product 1

HCID 1557781-Methyl-4-(3-methoxyphenyl)-1,2,3,6-tetrahydropyridine

Reagents, catalysts & solvents 1

HCID 6395Methanesulfonic AcidSolvent

Procedure

To a stirred solution of 200 ml. of 50 g. of phosphorous pentoxide in methanesulfonic acid was added portionwise over four minutes 59 g. of 1-methyl-4-hydroxy-4-(3-hydroxyphenyl)piperidine. The reaction was exothermic, the temperature rising to 70° C. After complete addition of the piperidine derivative, the reaction mixture was poured onto 200 g. of ice, and the resulting aqueous mixture made alkaline by theaddition of ammonium hydroxide. The alkaline mixture was extracted several times with diethyl ether, and the ethereal extracts were combined, washed with water, dried, and the solvent removed by evaporation under reduced pressure to provide 44.7 g. of an oil. The oil was distilled to provide 1-methyl-4-(3-methoxyphenyl)-1,2,5,6-tetrahydropyridine; B.P.=123°-138° C. at 0.1 torr.

Workup

  1. customrising to 70° C
  2. additionthe reaction mixture was poured onto 200 g
  3. extractionThe alkaline mixture was extracted several times with diethyl ether
  4. washwashed with water
  5. customdried
  6. customthe solvent removed by evaporation under reduced pressure
  7. customto provide 44.7 g
  8. distillationThe oil was distilled

Sources & evidence

ORD record
ord-0601159aaeb44113a697b4c1f4a39069
Source dataset
uspto-grants-1981_07
Patent number
US04277608

Reaction notes

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