Acetone → HCID 131716769, compound

HRID 1886407Notes

Reaction equation

HRID 1886407 reaction equation
[CH3:1][C:2]1[O:6][C:5]([CH2:7][N:8]2[C:12]3[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=3[N:10]=[C:9]2[NH:17][CH:18]2[CH2:24][CH2:23][CH2:22][N:21](C(OCC)=O)[CH2:20][CH2:19]2)=[CH:4][CH:3]=1.[OH-:30].[K+].[OH2:32].CC(=[O:36])C>>[C:5]([OH:6])(=[O:36])/[CH:4]=[CH:3]/[C:2]([OH:32])=[O:30].[NH:21]1[CH2:22][CH2:23][CH2:24][CH:18]([NH:17][C:9]2[N:8]([CH2:7][C:5]3[O:6][C:2]([CH3:1])=[CH:3][CH:4]=3)[C:12]3[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=3[N:10]=2)[CH2:19][CH2:20]1

Participants

5

Reactant 4

HCID 180AcetoneHCID 962WaterHCID 14797Potassium Hydroxide2×HCID 15037355HCID 15037355, compound

Product 1

HCID 131716769HCID 131716769, compoundYield 52.9%

Procedure

A mixture of 188 parts of ethyl hexahydro-4-[[1-[(5-methyl-2-furanyl)methyl]-1H-benzimidazol-2-yl]-amino]-1H-azepine-1-carboxylate, 166.5 parts of potassium hydroxide, 18 parts of water and 1440 parts of 2-propanone was stirred for 18 hours at reflux temperature. After cooling, another portion of 166.5 parts of potassium hydroxide was added and stirring was continued for 6 hours at reflux. After cooling, the reaction mixture was evaporated and the residue was stirred in 1500 parts of water. The product was extracted three times with dichloromethane. The extract was dried, filtered and evaporated. The residue was converted into the (E)-2-butenedioate salt in 2000 parts of 2-propanone and 800 parts of ethanol. The reaction mixture was allowed to cool while stirring. The precipitated product was filtered off, washed with 2-propanone and crystallized from a mixture of 2-propanone and ethanol (1:2 by volume). The product was filtered off, washed with 2-propanone and dried in vacuo at 50° C., yielding 132.6 parts (52.9%) of N-(hexahydro-1H-azepin-4-yl)-1-[(5-methyl-2-furanyl)methyl]-1H-benzimidazol-2-amine (E)-2-butenedioate(2:3).trihydrate; mp. 115.2° C. (compound 48).

Workup

  1. temperatureat reflux temperature
  2. temperatureAfter cooling
  3. stirringstirring
  4. waitwas continued for 6 hours
  5. temperatureat reflux
  6. temperatureAfter cooling
  7. customthe reaction mixture was evaporated
  8. stirringthe residue was stirred in 1500 parts of water
  9. extractionThe product was extracted three times with dichloromethane
  10. customThe extract was dried
  11. filtrationfiltered
  12. customevaporated
  13. temperatureto cool
  14. stirringwhile stirring
  15. filtrationThe precipitated product was filtered off
  16. washwashed with 2-propanone
  17. customcrystallized from a mixture of 2-propanone and ethanol (1:2 by volume)
  18. filtrationThe product was filtered off
  19. washwashed with 2-propanone
  20. customdried in vacuo at 50° C.

Sources & evidence

ORD record
ord-80b77e7d14e34a66b37e8f56aa04c1d4
Source dataset
uspto-grants-1992_09
Patent number
US05151424

Reaction notes

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