Water → HCID 131716771, compound

HRID 704731Notes

Reaction equation

HRID 704731 reaction equation
[OH-:1].[K+].[OH2:3].[CH3:4][C:5]1[O:9][C:8]([CH2:10][N:11]2[C:15]3[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=3[N:13]=[C:12]2[NH:20][CH:21]2[CH2:27][CH2:26][CH2:25][N:24]([CH2:28][CH2:29][NH:30]C(=O)OCC)[CH2:23][CH2:22]2)=[CH:7][CH:6]=1.CC([OH:39])C>>[C:8]([OH:9])(=[O:39])/[CH:7]=[CH:6]/[C:5]([OH:3])=[O:1].[NH2:30][CH2:29][CH2:28][N:24]1[CH2:25][CH2:26][CH2:27][CH:21]([NH:20][C:12]2[N:11]([CH2:10][C:8]3[O:9][C:5]([CH3:4])=[CH:6][CH:7]=3)[C:15]3[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=3[N:13]=2)[CH2:22][CH2:23]1

Participants

5

Reactant 4

HCID 962WaterHCID 3776IsopropanolHCID 14797Potassium HydroxideHCID 15037509HCID 15037509, compound

Product 1

HCID 131716771HCID 131716771, compoundYield 55.8%

Procedure

To a stirred mixture of 85 parts of potassium hydroxide, 5 parts of water and 368 parts of 2-propanol were added 50.5 parts of ethyl [2-[hexahydro-4-[[1-[(5-methyl-2-furanyl)methyl]-1H-benzimidazol-2-yl]amino]-1H-azepin-1-yl]ethyl]carbamate (exothermic reaction, the mixture was cooled when the temperature reached 60° C.). The reaction mixture was refluxed for 2 hours. After cooling, the mixture was evaporated. The residue was taken up in 800 parts of water and the product was extracted three times with dichloromethane. The combined extracts were washed with a small amount of water, dried, filtered and evaporated. The residue was converted into the (E)-2-butenedioate salt in 320 parts of ethanol. The salt was filtered off, washed with ethanol and dried in vacuo at 40° C., yielding 48.0 parts (55.8%) of N-[1-(2-aminoethyl)hexahydro-1H-azepin-4-yl]-1-[(5-methyl-2-furanyl)methyl]-1H-benzimidazol-2-amine (E)-2-butenedioate(1:3); mp. ≥145° C. (compound 149).

Workup

  1. customexothermic reaction
  2. temperaturethe mixture was cooled when the temperature
  3. customreached 60° C.
  4. temperatureThe reaction mixture was refluxed for 2 hours
  5. temperatureAfter cooling
  6. customthe mixture was evaporated
  7. extractionthe product was extracted three times with dichloromethane
  8. washThe combined extracts were washed with a small amount of water
  9. customdried
  10. filtrationfiltered
  11. customevaporated
  12. filtrationThe salt was filtered off
  13. washwashed with ethanol
  14. customdried in vacuo at 40° C.

Sources & evidence

ORD record
ord-2c064300dc2749b7a8563f2556d4c14c
Source dataset
uspto-grants-1991_01
Patent number
US04988689

Reaction notes

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