[Benzo[b]thiophene-2-yl][1-(2-phenylethyl)-4-piperidinyl]methanone → alpha-[1-(2-Phenylethyl)-4-piperidinyl]-alpha-phenyl-2-benzo[b]thiophenemethanol

HRID 1491694

반응식

HRID 1491694 반응식
[S:1]1[C:5]([C:6]([CH:8]2[CH2:13][CH2:12][N:11]([CH2:14][CH2:15][C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[CH2:10][CH2:9]2)=[O:7])=[CH:4][C:3]2[CH:22]=[CH:23][CH:24]=[CH:25][C:2]1=2.[C:26]1([Li])[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1>O1CCCC1.C1CCCCC1.C(OCC)C>[C:16]1([CH2:15][CH2:14][N:11]2[CH2:12][CH2:13][CH:8]([C:6]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)([C:5]3[S:1][C:2]4[CH:25]=[CH:24][CH:23]=[CH:22][C:3]=4[CH:4]=3)[OH:7])[CH2:9][CH2:10]2)[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1

참가 물질

5

반응물 2

HCID 18930331[Benzo[b]thiophene-2-yl][1-(2-phenylethyl)-4-piperidinyl]methanoneHCID 178506676HCID 178506676, 화합물

생성물 1

HCID 18930373alpha-[1-(2-Phenylethyl)-4-piperidinyl]-alpha-phenyl-2-benzo[b]thiophenemethanol

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매HCID 21895417Cyclohexane diethylether용매

반응 조건

온도
-78 °C

실험 절차

Dissolve [benzo[b]thiophene-2-yl][1-(2-phenylethyl)-4-piperidinyl]methanone (3.5 g, 10.01 mmol) in anhydrous tetrahydrofuran (100 mL), place under an argon atmosphere and cool to -78° C. Add, by dropwise addition, phenyllithium (6 mL of a 2.0M solution in cyclohexane/ethyl ether, 12.0 mmol) and stir at -78° C. for 5 hours. Remove the ice bath and allow to warm to room temperature. Pour into saturated ammonium chloride (100 mL) and stir for 20 minutes. Separate the organic phase and extract the aqueous phase with ethyl acetate. Combine the organic phases, wash with water, dry (MgSO4) and evaporate the solvent in vacuo. Purify by chromatography (50% ethyl acetate/hexane) and recrystallize (isopropanol) to give the title compound as a white solid; mp 144°-146° C.

후처리

  1. customRemove the ice bath
  2. temperatureto warm to room temperature
  3. additionPour into saturated ammonium chloride (100 mL)
  4. stirringstir for 20 minutes
  5. customSeparate the organic phase
  6. extractionextract the aqueous phase with ethyl acetate
  7. washwash with water
  8. dry with materialdry (MgSO4)
  9. customevaporate the solvent in vacuo
  10. customPurify by chromatography (50% ethyl acetate/hexane)
  11. customrecrystallize (isopropanol)

출처 및 근거

ORD 기록
ord-54b5cc5b5e4146fb83c240bf0d6d954d
출처 데이터셋
uspto-grants-1994_12
특허 번호
US05371093

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