Water → HCID 131716480, compound

HRID 2166145Notes

Reaction equation

HRID 2166145 reaction equation
[CH2:1]([O:3][CH2:4][CH2:5][N:6]1[CH2:11][CH2:10][CH:9]([NH:12][C:13]2[NH:17][C:16]3[CH:18]=[CH:19][CH:20]=[CH:21][C:15]=3[N:14]=2)[CH2:8][CH2:7]1)[CH3:2].[H-].[Na+].Cl[CH2:25][CH2:26][O:27][CH2:28][CH3:29].[OH2:30].CN(C)[CH:33]=[O:34]>>[C:33]([OH:34])(=[O:27])[C:4]([OH:3])=[O:30].[CH2:26]([O:27][CH2:28][CH2:29][N:17]1[C:16]2[CH:18]=[CH:19][CH:20]=[CH:21][C:15]=2[N:14]=[C:13]1[NH:12][CH:9]1[CH2:8][CH2:7][N:6]([CH2:5][CH2:4][O:3][CH2:1][CH3:2])[CH2:11][CH2:10]1)[CH3:25]

Participants

6

Reactant 5

HCID 962WaterHCID 6228Dimethylformamide2×HCID 12341Ethane, 1-chloro-2-ethoxy-HCID 24758Sodium hydrideHCID 15718790HCID 15718790, compound

Product 1

HCID 131716480HCID 131716480, compoundYield 39.5%

Procedure

To a stirred mixture of 4.32 parts of N-[1-(2-ethoxyethyl)-4-piperidinyl]-1H-benzimidazol-2-amine and 135 parts of N,N-dimethylformamide were added 0.75 parts of a sodium hydride dispersion 50% under nitrogen atmosphere. After stirring for 30 minutes at room temperature, a solution of 1.63 parts of 1-chloro-2-ethoxyethane in N,N-dimethylformamide was added dropwise to the thus obtained mixture at 50° C. Upon complete addition, stirring was continued overnight at 50° C. The reaction mixture was poured into water and the product was extracted with 4-methyl-2-pentanone. The extract was dried, filtered and evaporated. The residue was purified by column chromatography over silica gel using a mixture of trichloromethane and methanol, saturated with ammonia, (98:2 by volume) as eluent. The pure fractions were collected and the eluent was evaporated. The residue was converted into the ethanedioate salt in ethanol. The salt was filtered off and dried, yielding 3.2 parts (39.5%) of 1-(2-ethoxyethyl)-N-[1-(2-ethoxyethyl)-4-piperidinyl]-1H-benzimidazol-2-amine ethanedioate(1:2); mp. 184.7° C. (compound 153).

Workup

  1. additionUpon complete addition
  2. stirringstirring
  3. waitwas continued overnight at 50° C
  4. extractionthe product was extracted with 4-methyl-2-pentanone
  5. customThe extract was dried
  6. filtrationfiltered
  7. customevaporated
  8. customThe residue was purified by column chromatography over silica gel using
  9. additiona mixture of trichloromethane and methanol
  10. customThe pure fractions were collected
  11. customthe eluent was evaporated
  12. filtrationThe salt was filtered off
  13. customdried

Sources & evidence

ORD record
ord-4512b8f2ded74ea6b9062e7b05699e44
Source dataset
uspto-grants-1990_07
Patent number
US04943580

Reaction notes

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