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

HRID 225220Notes

Reaction equation

HRID 225220 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 the addition 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-d1062ece720f40ceab4c35e4c4b504ce
Source dataset
uspto-grants-1980_11
Patent number
US04236009

Reaction notes

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