alpha,alpha-Bis(4-methoxyphenyl)-1-(phenylmethyl)-4-piperidinemethanol → alpha,alpha-Bis(4-methoxyphenyl)-4-piperidinemethanol

HRID 476927노트

반응식

HRID 476927 반응식
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]([C:24]2[CH:29]=[CH:28][C:27]([O:30][CH3:31])=[CH:26][CH:25]=2)([CH:11]2[CH2:16][CH2:15][N:14](CC3C=CC=CC=3)[CH2:13][CH2:12]2)[OH:10])=[CH:5][CH:4]=1>C(O)C.[Pd]>[CH3:31][O:30][C:27]1[CH:28]=[CH:29][C:24]([C:9]([C:6]2[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:8][CH:7]=2)([CH:11]2[CH2:16][CH2:15][NH:14][CH2:13][CH2:12]2)[OH:10])=[CH:25][CH:26]=1

참가 물질

4

반응물 1

HCID 14698738alpha,alpha-Bis(4-methoxyphenyl)-1-(phenylmethyl)-4-piperidinemethanol

생성물 1

HCID 14698742alpha,alpha-Bis(4-methoxyphenyl)-4-piperidinemethanol수율 30%

시약·촉매·용매 2

HCID 23938Palladium촉매HCID 702Ethanol용매

실험 절차

A solution of 36.7 g (0.088 mole) of α,α-bis(4-methoxyphenyl)-1-(phenylmethyl)-4-piperidinemethanol in 500 ml of absolute ethanol was hydrogenated over palladium on carbon at 60° C. in a Parr apparatus over the weekend. The mixture was cooled, filtered through Celite®, fresh catalyst added to the filtrate and the mixture hydrogenated. This process was repeated so that no starting material was present by mass spectral analysis. The filtrate was concentrated and the residue was partitioned between methylene chloride and a 5% sodium hydroxide solution. The organic layer was dried over sodium sulfate and concentrated to give a solid residue. The solid was recrystallized from 2-propanol to yield 8.6 g (30%) of white solid, m.p. 153°-155° C.

후처리

  1. temperatureThe mixture was cooled
  2. filtrationfiltered through Celite®, fresh catalyst
  3. additionadded to the filtrate
  4. concentrationThe filtrate was concentrated
  5. customthe residue was partitioned between methylene chloride
  6. dry with materialThe organic layer was dried over sodium sulfate
  7. concentrationconcentrated
  8. customto give a solid residue
  9. customThe solid was recrystallized from 2-propanol

출처 및 근거

ORD 기록
ord-8f10401068eb4c418b7ca6a7b8fa195f
출처 데이터셋
uspto-grants-1989_12
특허 번호
US04886794

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