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

HRID 851134
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인쇄 미리보기

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HRID 851134 반응식
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
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 962
Water
용매
HCID 8857Ethyl Acetate용매

반응 조건

온도
140 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-b96df321c70041cc925d100de1204379
출처 데이터셋
uspto-grants-1983_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US04382942

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