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

HRID 441403

反応式

HRID 441403 の反応式
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]

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-927041b00c9243889702d8e1c647dfc7
出典データセット
uspto-grants-1977_08
特許番号
US04039670

関連ノート

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