1-Butanol → HCID 131716473, compound

HRID 2166131Notes

Reaction equation

HRID 2166131 reaction equation
N1C=CC=NC=1[O:7][CH2:8][CH2:9][N:10]1[C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=2[N:12]=[C:11]1[NH:19][CH:20]1[CH2:26][CH2:25][CH2:24][N:23](C(OCC)=O)[CH2:22][CH2:21]1.[CH2:32]([OH:36])[CH2:33][CH2:34][CH3:35].[OH-:37].[K+].[OH2:39]>>[C:32]([OH:7])(=[O:36])/[CH:33]=[CH:34]/[C:35]([OH:39])=[O:37].[NH:23]1[CH2:24][CH2:25][CH2:26][CH:20]([NH:19][C:11]2[N:10]([CH2:9][CH2:8][OH:7])[C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=3[N:12]=2)[CH2:21][CH2:22]1

Participants

5

Reactant 4

HCID 2631-ButanolHCID 962Water2×HCID 14797Potassium HydroxideHCID 15718833HCID 15718833, compound

Product 1

HCID 131716473HCID 131716473, compoundYield 38.5%

Procedure

A mixture of 27 parts of ethyl hexahydro-4-[[1-[2-(2-pyrimidinyloxy)ethyl]-1H-benzimidazol-2-yl]amino]-1H-azepine-1-carboxylate, 160 parts of 1-butanol, 28 parts of potassium hydroxide and 2 parts of water was stirred overnight at reflux temperature. The reaction mixture was diluted with water and the whole was extracted with 1-butanol. The extract was dried, filtered and evaporated. The residue was taken up in water and the product was extracted with dichloromethane. The extract was dried, filtered and evaporated. The residue was converted into the (E)-2-butenedioate salt in ethanol. The salt was filtered off and dried, yielding 9.77 parts (38.5%) of 2-[(hexahydro-1H-azepin-4-yl)amino]-1H-benzimidazole-1-ethanol (E)-2-butenedioate(1:2); mp. 176.1° C. (compound 35).

Workup

  1. temperatureat reflux temperature
  2. extractionthe whole was extracted with 1-butanol
  3. customThe extract was dried
  4. filtrationfiltered
  5. customevaporated
  6. extractionthe product was extracted with dichloromethane
  7. customThe extract was dried
  8. filtrationfiltered
  9. customevaporated
  10. filtrationThe salt was filtered off
  11. customdried

Sources & evidence

ORD record
ord-49dc5b5f806f4194875a2018458f220e
Source dataset
uspto-grants-1990_07
Patent number
US04943580

Reaction notes

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