Piperidine → 1,2,3,6-Tetrahydro-4-(3-methoxyphenyl)-1-methylpyridine

HRID 1277523노트

반응식

HRID 1277523 반응식
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

참가 물질

6

반응물 4

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

생성물 1

HCID 1557781,2,3,6-Tetrahydro-4-(3-methoxyphenyl)-1-methylpyridine

시약·촉매·용매 1

HCID 6395Methanesulfonic Acid용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-0601159aaeb44113a697b4c1f4a39069
출처 데이터셋
uspto-grants-1981_07
특허 번호
US04277608

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