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

HRID 1736433

반응식

HRID 1736433 반응식
[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

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
90 °C

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-d32c1cb8f02c490683939e8dda47f6dc
출처 데이터셋
uspto-grants-1996_07
특허 번호
US05541200

연결된 노트

불러오는 중…