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

HRID 327028

Reaction equation

HRID 327028 reaction equation
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

Participants

6

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

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:

Workup

  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)

Sources & evidence

ORD record
ord-788b481de1f94d69a8e058708303766f
Source dataset
uspto-grants-1993_12
Patent number
US05272150

Linked notes

Loading…