Iodine → 1-Benzyl-3-(3-trifluoromethyl-phenyl)-piperidine-3-ol

HRID 354836ノート

反応式

HRID 354836 の反応式
[Mg].II.Br[C:5]1[CH:6]=[C:7]([C:11]([F:14])([F:13])[F:12])[CH:8]=[CH:9][CH:10]=1.[CH2:15]([N:22]1[CH2:27][CH2:26][CH2:25][C:24](=[O:28])[CH2:23]1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>CCOCC>[CH2:15]([N:22]1[CH2:27][CH2:26][CH2:25][C:24]([OH:28])([C:5]2[CH:10]=[CH:9][CH:8]=[C:7]([C:11]([F:14])([F:13])[F:12])[CH:6]=2)[CH2:23]1)[C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1

参加物

6

反応物 4

HCID 807IodineHCID 9817Benzene, 1-bromo-3-(trifluoromethyl)-HCID 966503-Piperidinone, 1-(phenylmethyl)-HCID 5462224Magnesium

生成物 1

HCID 205064151-Benzyl-3-(3-trifluoromethyl-phenyl)-piperidine-3-ol

試薬・触媒・溶媒 1

HCID 3283Diethyl Ether溶媒3 回

実験手順

Under anhydrous conditions, to a mixture of 11 g. of magnesium in 15 ml. of ethyl ether an iodine crystal is added followed by the addition of a solution of 100 g. of m-bromotrifluoromethylbenzene in 300 ml. of ether over a two hour period. The resulting mixture is stirred for two hours at ambient temperature then cooled to 5° C. A solution of 70 g. of N-benzyl-3-piperidone in 300 ml. of ether is added at this temperature over one hour. After stirring for 15 minutes at 5° C. and one hour at 20°-25° C., the reaction mixture was poured onto 800 ml. of ice-water with stirring. The mixture is filtered, the organic layer extracted with 4×100 ml. of 1 N hydrochloric acid and once with brine. The aqueous phase is made alkaline by addition of triethylamine in the cold and the resulting mixture extracted with ethyl acetate. The combined extracts are washed with brine, dried (MgSO4) and evaporated to dryness. The crude product is purified by silica gel chromatography, eluting with cyclohexane/chloroform/triethylamine (85:10:5 by volume) to obtain the desired product as an orange colored solid.

後処理

  1. additionUnder anhydrous conditions, to a mixture of 11 g
  2. additionfollowed by the addition of a solution of 100 g
  3. temperaturethen cooled to 5° C
  4. stirringAfter stirring for 15 minutes at 5° C. and one hour at 20°-25° C.
  5. additionthe reaction mixture was poured onto 800 ml
  6. filtrationThe mixture is filtered
  7. extractionthe organic layer extracted with 4×100 ml
  8. additionby addition of triethylamine in the cold and the resulting mixture
  9. extractionextracted with ethyl acetate
  10. washThe combined extracts are washed with brine
  11. dry with materialdried (MgSO4)
  12. customevaporated to dryness
  13. customThe crude product is purified by silica gel chromatography
  14. washeluting with cyclohexane/chloroform/triethylamine (85:10:5 by volume)

出典と根拠

ORDレコード
ord-fc3d377e13f8459aa5ea310dbfecdd61
出典データセット
uspto-grants-1983_03
特許番号
US04377581

反応ノート

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