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

HRID 345471ノート

反応式

HRID 345471 の反応式
[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

参加物

4

反応物 1

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 23938Palladium触媒HCID 702Ethanol溶媒

実験手順

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 1 tsp of 5% Pd/C 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 process repeated until 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, mp 153°-155° C.

後処理

  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

出典と根拠

ORDレコード
ord-207f2d00f0d24fbea7a2b5824d3b3ab4
出典データセット
uspto-grants-1991_10
特許番号
US05057524

反応ノート

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