[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

反応式

HRID 1491694 の反応式
[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

参加物

5

反応物 2

HCID 18930331[Benzo[b]thiophene-2-yl][1-(2-phenylethyl)-4-piperidinyl]methanoneHCID 178506676HCID 178506676、化合物

生成物 1

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

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒HCID 21895417Cyclohexane diethylether溶媒

反応条件

温度
-78 °C

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-54b5cc5b5e4146fb83c240bf0d6d954d
出典データセット
uspto-grants-1994_12
特許番号
US05371093

関連ノート

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