Water → 1-[(2-Methoxy-3-pyridyl)methyl]-4-[2-oxo-2-(2-trifluoroacetylaminophenyl)ethyl]piperidine

HRID 1837737ノート

反応式

HRID 1837737 の反応式
Br[C:2]1[CH:14]=[CH:13][CH:12]=[CH:11][C:3]=1[NH:4][C:5](=[O:10])[C:6]([F:9])([F:8])[F:7].C([Li])(C)(C)C.CON(C)[C:23](=[O:40])[CH2:24][CH:25]1[CH2:30][CH2:29][N:28]([CH2:31][C:32]2[C:33]([O:38][CH3:39])=[N:34][CH:35]=[CH:36][CH:37]=2)[CH2:27][CH2:26]1.O>O1CCCC1.C(OCC)C>[CH3:39][O:38][C:33]1[C:32]([CH2:31][N:28]2[CH2:27][CH2:26][CH:25]([CH2:24][C:23](=[O:40])[C:2]3[CH:14]=[CH:13][CH:12]=[CH:11][C:3]=3[NH:4][C:5](=[O:10])[C:6]([F:9])([F:8])[F:7])[CH2:30][CH2:29]2)=[CH:37][CH:36]=[CH:35][N:34]=1

参加物

7

反応物 4

HCID 962WaterHCID 4263215N-(2-Bromophenyl)-2,2,2-trifluoroacetamideHCID 22678599N1-Methoxy,N1-methyl-2-[1-[(2-methoxy-3-pyridyl)methyl]-4-piperidyl]acetamideHCID 178418306HCID 178418306、化合物

生成物 1

HCID 226786181-[(2-Methoxy-3-pyridyl)methyl]-4-[2-oxo-2-(2-trifluoroacetylaminophenyl)ethyl]piperidine

試薬・触媒・溶媒 2

HCID 3283Diethyl Ether溶媒2 回HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
-78 °C

実験手順

482 mg of 2-bromo-N-(trifluoroacetyl)aniline was dissolved in a mixed solvent of 1.8 ml of tetrahydrofuran and 1.8 ml of diethyl ether, and a 1.14M methyllithium diethyl ether solution was added dropwise thereinto at 0° C. After stirring for 10 minutes, the mixture was slowly charged by a cannular to a solution of 2.4 ml of 1.51 M tert-butyllithium and 4 ml of a diethyl ether solution cooled at −78° C. The mixture was stirred for 1 hour. Then, a mixed solution of 500 mg of N1-methoxy,N1-ethyl-2-[1-(2-methoxy-3-pyridyl)methyl]-4-piperidyl]acetamide obtained in Example 55 and 2 ml of tetrahydrofuran was added dropwise thereinto, and the mixture was further stirred for 20 minutes. Water was added to the reaction solution, and the mixture was extracted with ethyl acetate. The organic layer was washed with brine, and then dried over anhydrous magnesium sulfate. The solvent was evaporated, and the crude product was purified by silica gel column chromatography (ethyl acetate), to give 150 mg of the above compound as a yellow oil.

後処理

  1. customat 0° C
  2. stirringThe mixture was stirred for 1 hour
  3. stirringthe mixture was further stirred for 20 minutes
  4. extractionthe mixture was extracted with ethyl acetate
  5. washThe organic layer was washed with brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customThe solvent was evaporated
  8. customthe crude product was purified by silica gel column chromatography (ethyl acetate)

出典と根拠

ORDレコード
ord-5fe8433145b345158fc9d583bd99c979
出典データセット
uspto-grants-2004_08
特許番号
US06784192B2

反応ノート

読み込み中…