1-Bromo-3-chlorobenzene → 3-(3-Chlorophenyl)-1-(phenylmethyl)-3-piperidinol hydrochloride

HRID 359409ノート

反応式

HRID 359409 の反応式
Br[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[CH:3]=1.[Mg].O1CCCC1.[C:15]1([CH2:21][N:22]2[CH2:27][CH2:26][CH2:25][C:24](=[O:28])[CH2:23]2)[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>C(O)(=O)C>[ClH:8].[Cl:8][C:4]1[CH:3]=[C:2]([C:24]2([OH:28])[CH2:25][CH2:26][CH2:27][N:22]([CH2:21][C:15]3[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=3)[CH2:23]2)[CH:7]=[CH:6][CH:5]=1

参加物

6

反応物 4

HCID 79281-Bromo-3-chlorobenzeneHCID 8028TetrahydrofuranHCID 966503-Piperidinone, 1-(phenylmethyl)-HCID 5462224Magnesium

生成物 1

HCID 190955863-(3-Chlorophenyl)-1-(phenylmethyl)-3-piperidinol hydrochloride収率 76%

試薬・触媒・溶媒 1

HCID 176Acetic Acid溶媒

実験手順

To a stirred and refluxed Grignard complex previously prepared starting from a mixture of 4.2 parts of 1-bromo-3-chlorobenzene, 5.4 parts of magnesium and 135 parts of tetrahydrofuran were added dropwise 19 parts of 1-(phenylmethyl)-3-piperidinone. Upon completion, stirring was continued for 1 hour at reflux temperature. After cooling, the reaction mixture was poured into ice water and 12.5 parts of acetic acid. The layers were separated. The aqueous phase was extracted with trichloromethane. The organic layer was washed with water, dried, filtered and evaporated. The residue was converted into the hydrochloride salt in 2-propanol. The salt was filtered off and dried, yielding 26 parts (76%) of 3-(3-chlorophenyl)-1-(phenylmethyl)-3-piperidinol hydrochloride (intermediate 27).

後処理

  1. temperaturerefluxed Grignard complex
  2. custompreviously prepared
  3. stirringUpon completion, stirring
  4. temperatureat reflux temperature
  5. temperatureAfter cooling
  6. customThe layers were separated
  7. extractionThe aqueous phase was extracted with trichloromethane
  8. washThe organic layer was washed with water
  9. customdried
  10. filtrationfiltered
  11. customevaporated
  12. filtrationThe salt was filtered off
  13. customdried

出典と根拠

ORDレコード
ord-a077c131c37446cda95b2797740d3ca2
出典データセット
uspto-grants-1991_03
特許番号
US05001125

反応ノート

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