Potassium Iodide → 1-[gamma-(2-Methyl-4-fluorobenzoyl)-propyl]-4-(3-trifluoromethylphenyl)-4-hydroxypiperidine

HRID 441403

반응식

HRID 441403 반응식
Cl[CH2:2][CH2:3][CH2:4][C:5]1([C:10]2[CH:15]=[CH:14][C:13]([F:16])=[CH:12][C:11]=2[CH3:17])[O:9]CCO1.[F:18][C:19]([F:34])([F:33])[C:20]1[CH:21]=[C:22]([C:26]2([OH:32])[CH2:31][CH2:30][NH:29][CH2:28][CH2:27]2)[CH:23]=[CH:24][CH:25]=1.C(=O)([O-])[O-].[K+].[K+].[I-].[K+]>CN(C)C=O>[CH3:17][C:11]1[CH:12]=[C:13]([F:16])[CH:14]=[CH:15][C:10]=1[C:5]([CH2:4][CH2:3][CH2:2][N:29]1[CH2:28][CH2:27][C:26]([C:22]2[CH:23]=[CH:24][CH:25]=[C:20]([C:19]([F:18])([F:33])[F:34])[CH:21]=2)([OH:32])[CH2:31][CH2:30]1)=[O:9]

참가 물질

6

반응물 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 752554-[3-(Trifluoromethyl)phenyl]-4-piperidinolHCID 130029542-(3-Chloropropyl)-2-(4-fluoro-2-methylphenyl)-1,3-dioxolane

생성물 1

HCID 130029551-[gamma-(2-Methyl-4-fluorobenzoyl)-propyl]-4-(3-trifluoromethylphenyl)-4-hydroxypiperidine

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

A mixture of 3 g of 4-chloro-1-(2-methyl-4-fluorophenyl)-1,1-ethylenedioxybutane, 2.5 g of 4-(3-trifluoromethylphenyl)-4-hydroxypiperidine, 1,4 g of anhydrous potassium carbonate, 0.05 g of potassium iodide and 30 ml of dimethylformamide was refluxed for 3 hours. The resulting mixture was poured into ice water and was extracted with ethyl acetate. The extract was washed with water, dried over anhydrous sodium sulfate and concentrated in vacuo. To the residual oil were added 60 ml of methanol, 21 ml of water and 10.5 ml of concentrated hydrochloric acid. The mixture was refluxed for 50 minutes and concentrated in vacuo. The residual oil was made alkaline with 28 % aqueous ammonia and extracted with ethyl acetate. The extract was washed with water, dried over anhydrous sodium sulfate and concentrated. The residual solid was recrystallized from isopropyl ether to give 1-[γ-(2-methyl-4-flourobenzoyl)-propyl]-4-(3-trifluoromethylphenyl)-4-hydroxypiperidine, melting at about 63.5°-64.5+ C.

후처리

  1. temperaturewas refluxed for 3 hours
  2. extractionwas extracted with ethyl acetate
  3. washThe extract was washed with water
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated in vacuo
  6. additionTo the residual oil were added 60 ml of methanol, 21 ml of water and 10.5 ml of concentrated hydrochloric acid
  7. temperatureThe mixture was refluxed for 50 minutes
  8. concentrationconcentrated in vacuo
  9. extractionextracted with ethyl acetate
  10. washThe extract was washed with water
  11. dry with materialdried over anhydrous sodium sulfate
  12. concentrationconcentrated
  13. customThe residual solid was recrystallized from isopropyl ether

출처 및 근거

ORD 기록
ord-927041b00c9243889702d8e1c647dfc7
출처 데이터셋
uspto-grants-1977_08
특허 번호
US04039670

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