Trifluoroacetic acid → [Benzo[b]thiophene-3-yl][1-[2-(4-methoxyphenyl)ethyl]-4-piperidinyl]methanone

HRID 266082ノート

反応式

HRID 266082 の反応式
[S:1]1[CH:5]=[C:4]([C:6]([CH:8]2[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]2)=[O:7])[C:3]2[CH:14]=[CH:15][CH:16]=[CH:17][C:2]1=2.C(C(O)=O)(F)(F)F.[CH3:25][O:26][C:27]1[CH:32]=[CH:31][C:30]([CH2:33][CH2:34]Br)=[CH:29][CH:28]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[S:1]1[CH:5]=[C:4]([C:6]([CH:8]2[CH2:9][CH2:10][N:11]([CH2:34][CH2:33][C:30]3[CH:31]=[CH:32][C:27]([O:26][CH3:25])=[CH:28][CH:29]=3)[CH2:12][CH2:13]2)=[O:7])[C:3]2[CH:14]=[CH:15][CH:16]=[CH:17][C:2]1=2

参加物

6

反応物 4

HCID 6422Trifluoroacetic acidHCID 11430Potassium CarbonateHCID 844271-(2-Bromoethyl)-4-methoxybenzeneHCID 15337457(Benzo[b]thiophene-3-yl)(4-piperidinyl)methanone

生成物 1

HCID 9799982[Benzo[b]thiophene-3-yl][1-[2-(4-methoxyphenyl)ethyl]-4-piperidinyl]methanone

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
90 °C

実験手順

Mix (benzo[b]thiophene-3-yl)(4-piperidinyl)methanone.CF3CO2H (2.0 g, 5.56 mmol), 2-(4-methoxyphenyl)ethyl bromide (1.27 g, 5.93 mmol), potassium carbonate (1.95 g, 1.41 mmol) and anhydrous dimethylformamide (20 mL). Warm to approximately 90° C. and stir overnight. Allow to cool to room temperature and partition between a 2:1 mixture of ethyl acetate:toluene and water. Separate the aqueous phase and wash the organic phase with water and saturated sodium chloride. Dry (Na2SO4) and evaporate the solvent in vacuo. Purify by chromatography (40% ethyl acetate/hexane) and recrystallize (cyclohexane) to give the title compound as pale yellow plates; mp 114°-116° C.

後処理

  1. temperatureto cool to room temperature
  2. custompartition between a 2:1 mixture of ethyl acetate
  3. customSeparate the aqueous phase
  4. washwash the organic phase with water and saturated sodium chloride
  5. dry with materialDry (Na2SO4)
  6. customevaporate the solvent in vacuo
  7. customPurify by chromatography (40% ethyl acetate/hexane)
  8. customrecrystallize (cyclohexane)

出典と根拠

ORDレコード
ord-a0854de9e6f74a889369e73b3d2fc445
出典データセット
uspto-grants-1997_07
特許番号
US05650416

反応ノート

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