HCID 18930331、化合物 → alpha-[1-(2-Phenylethyl)-4-piperidinyl]-alpha-phenyl-2-benzo[b]thiophenemethanol

HRID 266097

反応式

HRID 266097 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 18930331HCID 18930331、化合物HCID 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-0c77f6a877e1492fae78aaf9ed602a09
出典データセット
uspto-grants-1997_07
特許番号
US05650416

関連ノート

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