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Dimethylformamide → [1-[(4-Fluorophenyl)methyl]-1H-benzimidazol-2-yl][1-[2-(4-methoxyphenyl)ethyl]-4-piperidinyl]methanone

HRID 1165212
ノート
印刷プレビュー

反応式

HRID 1165212 の反応式
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][N:9]2[C:13]3[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=3[N:11]=[C:10]2[C:18]([CH:20]2[CH2:25][CH2:24][NH:23][CH2:22][CH2:21]2)=[O:19])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].CN(C=O)C.Br[CH2:38][CH2:39][C:40]1[CH:45]=[CH:44][C:43]([O:46][CH3:47])=[CH:42][CH:41]=1>C1(C)C=CC=CC=1.C(OCC)(=O)C.O>[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][N:9]2[C:13]3[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=3[N:11]=[C:10]2[C:18]([CH:20]2[CH2:25][CH2:24][N:23]([CH2:38][CH2:39][C:40]3[CH:45]=[CH:44][C:43]([O:46][CH3:47])=[CH:42][CH:41]=3)[CH2:22][CH2:21]2)=[O:19])=[CH:4][CH:3]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

8

反応物 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 844271-(2-Bromoethyl)-4-methoxybenzeneHCID 155428834-(1-(4-fluorobenzyl)-1H-benzimidazole-2-carbonyl)piperidine

生成物 1

HCID 10917690[1-[(4-Fluorophenyl)methyl]-1H-benzimidazol-2-yl][1-[2-(4-methoxyphenyl)ethyl]-4-piperidinyl]methanone

試薬・触媒・溶媒 3

HCID 962
Water
溶媒
HCID 1140Toluene溶媒
HCID 8857Ethyl Acetate溶媒

実験手順

To a stirred, room temperature, mixture of [1-[(4-fluorophenyl)methyl]-1H-benzimidazol-2-yl]-4-piperidinylmethanone, mono (trifluoroacetate) (1.82 g, 4.03×10-3 mole), potassium carbonate (1.39 g, 1.00×10-2 mole), and sieve dry DMF (15 ml) was added 1-(2-bromoethyl)-4-methoxybenzene (0.87 g, 4.04×10-3 mole). The reaction was then immersed in an oil bath which had been preheated to ca. 90° C. After being stirred at between 80°-90° C. for 22 hours, the reaction was allowed to cool to room temperature. The reaction was poured into a separatory funnel containing H2O and a 2:1 mixture of ethyl acetate:toluene. The two phases were mixed and the aqueous layer was separated. The organic layer was washed two times with H2O and once with saturated aqueous NaCl before being dried over anhydrous Na2SO4. The drying agent was removed by filtration and the filtrate was evaporated at reduced pressure leaving an oil which was purified by flash chromatography (ethyl acetate). Crystallization from cyclohexane afforded [1-[(4-fluorophenyl)methyl]-1H-benzimidazol-2-yl][1-[2-(4-methoxyphenyl)ethyl]-4-piperidinyl]methanone as off white matted needles: 1.08 g (5%). This material was spectroscopically identical with the previously described product of Example III.

後処理

  1. customThe reaction was then immersed in an oil bath
  2. customhad been preheated to ca. 90° C
  3. additionThe reaction was poured into a separatory funnel
  4. additionThe two phases were mixed
  5. customthe aqueous layer was separated
  6. washThe organic layer was washed two times with H2O
  7. dry with materialonce with saturated aqueous NaCl before being dried over anhydrous Na2SO4
  8. customThe drying agent was removed by filtration
  9. customthe filtrate was evaporated at reduced pressure
  10. customleaving an oil which
  11. customwas purified by flash chromatography (ethyl acetate)
  12. customCrystallization from cyclohexane

出典と根拠

ORDレコード
ord-f3eb0363ae6e4fefbcec591850ade827
出典データセット
uspto-grants-1990_03
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US04908372

反応ノート

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