Methane → α-[1-[2-(4-Methoxyphenyl)ethyl]-4-piperidinyl]-α-phenyl-2-benzothiazolemethanol

HRID 266093

反応式

HRID 266093 の反応式
[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[C:10]([CH:12]1[CH2:17][CH2:16][N:15]([CH2:18][CH2:19][C:20]2[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[CH:22][CH:21]=2)[CH2:14][CH2:13]1)=[O:11].[C:28]1([Li])[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1.C>O1CCCC1.C1CCCCC1.C(OCC)C.C(Cl)Cl>[CH3:27][O:26][C:23]1[CH:22]=[CH:21][C:20]([CH2:19][CH2:18][N:15]2[CH2:16][CH2:17][CH:12]([C:10]([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)([C:2]3[S:1][C:5]4[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=4[N:3]=3)[OH:11])[CH2:13][CH2:14]2)=[CH:25][CH:24]=1

参加物

7

反応物 3

HCID 297MethaneHCID 9842862[2-Benzothiazolyl][1-[2-(4-methoxyphenyl)ethyl]-4-piperidinyl)methanoneHCID 178506676HCID 178506676、化合物

生成物 1

HCID 18930344α-[1-[2-(4-Methoxyphenyl)ethyl]-4-piperidinyl]-α-phenyl-2-benzothiazolemethanol

試薬・触媒・溶媒 3

HCID 6344Dichloromethane溶媒HCID 8028Tetrahydrofuran溶媒HCID 21895417Cyclohexane diethylether溶媒

反応条件

温度
-78 °C

実験手順

Dissolve [2-benzothiazolyl][1-[2-(4-methoxyphenyl)ethyl]-4-piperidinyl]methanone (2.0 g, 5.26 mmol) in anhydrous tetrahydrofuran (50 mL), place under an argon atmosphere and cool to -78° C. Add, by dropwise addition, phenyllithium (3.16 mL of a 2.0M solution in cyclohexane/ethyl ether, 6.31 mmol). Stir at -78° C. for 30 minutes, quench with saturated ammonium chloride (100 mL), separate the organic phase and extract the aqueous phase with ethyl acetate. Combine the organic phases, dry (MgSO4) and evaporate the solvent in vacuo. Purify by chromatography (75% ethyl acetate/hexane) to give a yellow oil. Dissolve the oil in methylene chloride and treat with activated charcoal.

後処理

  1. customquench with saturated ammonium chloride (100 mL)
  2. customseparate the organic phase
  3. extractionextract the aqueous phase with ethyl acetate
  4. dry with materialdry (MgSO4)
  5. customevaporate the solvent in vacuo
  6. customPurify by chromatography (75% ethyl acetate/hexane)
  7. customto give a yellow oil

出典と根拠

ORDレコード
ord-89916258f28a42408349c04189ac3716
出典データセット
uspto-grants-1997_07
特許番号
US05650416

関連ノート

読み込み中…