Ethylene Glycol → HCID 131716474, compound

HRID 2166132Notes

Reaction equation

HRID 2166132 reaction equation
[CH2:1]([O:3][CH2:4][CH2:5][N:6]1[C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=2[N:8]=[C:7]1[NH:15][CH:16]1[CH2:22][CH2:21][CH2:20][N:19](C(OCC)=O)[CH2:18][CH2:17]1)[CH3:2].[OH-:28].[K+].[CH2:30]([OH:33])[CH2:31][OH:32]>>[C:30]([OH:3])(=[O:33])[C:31]([OH:32])=[O:28].[CH2:1]([O:3][CH2:4][CH2:5][N:6]1[C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=2[N:8]=[C:7]1[NH:15][CH:16]1[CH2:22][CH2:21][CH2:20][NH:19][CH2:18][CH2:17]1)[CH3:2]

Participants

4

Reactant 3

HCID 174Ethylene GlycolHCID 14797Potassium HydroxideHCID 15718799HCID 15718799, compound

Product 1

HCID 131716474HCID 131716474, compoundYield 9.9%

Procedure

A mixture of 105 parts of ethyl 4-[[1-(2-ethoxyethyl)-1H-benzimidazol-2-yl]amino]hexahydro-1H-azepine-1-carboxylate, 79 parts of potassium hydroxide and 833 parts of 1,2-ethanediol was stirred overnight at reflux temperature. The reaction mixture was distilled in vacuo and the residue was taken up in dichloromethane. The organic phase was filtered and the filtrate was evaporated. The residue was purified by column chromatography over silica gel using a mixture of trichloromethane and methanol (90:10 by volume) as eluent. The pure fractions were collected and the eluent was evaporated. The residue was converted into the ethanedioate salt. The salt was filtered off and crystallized from 2-propanol. The product was filtered off and dried, yielding 16.4 parts (9.9%) of 1-(2-ethoxyethyl)-N-(hexahydro-1H-azepin-4-yl)-1H-benzimidazol-2-amine ethanedioate(1:3), monohydrate (compound 37).

Workup

  1. temperatureat reflux temperature
  2. distillationThe reaction mixture was distilled in vacuo
  3. filtrationThe organic phase was filtered
  4. customthe filtrate was evaporated
  5. customThe residue was purified by column chromatography over silica gel using
  6. additiona mixture of trichloromethane and methanol (90:10 by volume) as eluent
  7. customThe pure fractions were collected
  8. customthe eluent was evaporated
  9. filtrationThe salt was filtered off
  10. customcrystallized from 2-propanol
  11. filtrationThe product was filtered off
  12. customdried

Sources & evidence

ORD record
ord-e4d6bbd783f547188c3c4c18440369b3
Source dataset
uspto-grants-1990_07
Patent number
US04943580

Reaction notes

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