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

HRID 1450433

반응식

HRID 1450433 반응식
[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

참가 물질

7

반응물 3

HCID 297MethaneHCID 9842862[2-Benzothiazolyl][1-[2-(4-methoxyphenyl)ethyl]-4-piperidinyl)methanoneHCID 178506676HCID 178506676, 화합물

생성물 1

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

시약·촉매·용매 3

HCID 6344Dichloromethane용매HCID 8028Tetrahydrofuran용매HCID 21895417Cyclohexane diethylether용매

반응 조건

온도
-78 °C

실험 절차

Dissolve [2-benzothiazolyl][1-[2-(4-methoxyphenyl)ethyl]-4piperidinyl]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.

후처리

  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

출처 및 근거

ORD 기록
ord-02ba4ab3b5fc4113948ac9c575a83229
출처 데이터셋
uspto-grants-1997_02
특허 번호
US05602147

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