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

HRID 466541

반응식

HRID 466541 반응식
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

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 176Acetic Acid용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-d4ed9c45e1264c8387b318ac81df2510
출처 데이터셋
uspto-grants-1992_10
특허 번호
US05157035

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