Dimethylformamide → ethyl 5-[[2-[[1-(phenylmethyl)-4-piperidinyl]methyl]-1H-benzimidazol-1-yl]methyl]-2-furancarboxylate

HRID 327028

반응식

HRID 327028 반응식
CN(C)C=O.[H-].[Na+].[C:8]1([CH2:14][N:15]2[CH2:20][CH2:19][CH:18]([CH2:21][C:22]3[NH:26][C:25]4[CH:27]=[CH:28][CH:29]=[CH:30][C:24]=4[N:23]=3)[CH2:17][CH2:16]2)[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.Cl[CH2:32][C:33]1[O:37][C:36]([C:38]([O:40][CH2:41][CH3:42])=[O:39])=[CH:35][CH:34]=1>O>[C:8]1([CH2:14][N:15]2[CH2:16][CH2:17][CH:18]([CH2:21][C:22]3[N:23]([CH2:32][C:33]4[O:37][C:36]([C:38]([O:40][CH2:41][CH3:42])=[O:39])=[CH:35][CH:34]=4)[C:24]4[CH:30]=[CH:29][CH:28]=[CH:27][C:25]=4[N:26]=3)[CH2:19][CH2:20]2)[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

참가 물질

6

반응물 4

HCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 263166Ethyl 5-(chloromethyl)-2-furancarboxylateHCID 140128452-[[1-(phenylmethyl)-4-piperidinyl]methyl]-1H-benzimidazole

생성물 1

HCID 19734408ethyl 5-[[2-[[1-(phenylmethyl)-4-piperidinyl]methyl]-1H-benzimidazol-1-yl]methyl]-2-furancarboxylate수율 86.7%

시약·촉매·용매 1

HCID 962Water용매

실험 절차

To 470 parts of N,N-dimethylformamide were added portionwise 17.3 parts of a dispersion of sodium hydride in mineral oil (50%) and 91.6 parts of 2-[[1-(phenylmethyl)-4-piperidinyl]methyl]-1H-benzimidazole (as prepared in Example 16 of U.S. Pat. No. 4,695,575) while stirring under a nitrogen atmosphere. After stirring for 1 hour, 67.9 parts of ethyl 5-chloromethyl-2-furancarboxylate were added dropwise while cooling. Stirring was continued for 1 hour and then water was added to the reaction mixture. The product was extracted with methylbenzene and the extract was washed with water, dried, filtered and evaporated. The residue was dried azeotropically with methylbenzene (2x), yielding 119 parts (86.7%) of ethyl 5-[[2-[[1-(phenylmethyl)-4-piperidinyl]methyl]-1H-benzimidazol-1-yl]methyl]-2-furancarboxylate (interm. 4). Following the same procedure and starting from the appropriate starting materials, there were also prepared:

후처리

  1. customas prepared in Example 16 of U.S
  2. stirringAfter stirring for 1 hour
  3. temperaturewhile cooling
  4. stirringStirring
  5. extractionThe product was extracted with methylbenzene
  6. washthe extract was washed with water
  7. customdried
  8. filtrationfiltered
  9. customevaporated
  10. dry with materialThe residue was dried azeotropically with methylbenzene (2x)

출처 및 근거

ORD 기록
ord-788b481de1f94d69a8e058708303766f
출처 데이터셋
uspto-grants-1993_12
특허 번호
US05272150

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