HCID 14625395, compound → HCID 136114327, compound

HRID 2107810Notes

Reaction equation

HRID 2107810 reaction equation
C([N:9]1[C:16]2=[N:17][C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=3[N:15]2[CH2:14][CH2:13][N:12]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH2:11][CH2:10]1)(=O)C1C=CC=CC=1>N>[C:24]1([N:12]2[CH2:13][CH2:14][N:15]3[C:16](=[N:17][C:18]4[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=43)[NH:9][CH2:10][CH2:11]2)[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Participants

3

Reactant 1

HCID 14625395HCID 14625395, compound

Product 1

HCID 136114327HCID 136114327, compound

Reagents, catalysts & solvents 1

HCID 222AmmoniaSolvent

Procedure

A mixture of 1-benzoyl-1,2,3,4,5,6-hexahydro-4-phenyl[1,3,6]triazocino[1,2-a]benzimidazole (10.00 g) from Example 2 and methanolic ammonia (1150 ml), presaturated at 0°, was stirred magnetically and heated in a sealed bomb at 100° for 4 days. The resulting cooled solution was filtered and the filtrate was evaporated to a syrup which crystallized. The residue was dissolved in dichloromethane-methanol and the solution was evaporated to a syrup. Crystallization from methanol gave crude titled product; wt. 5.24 g (72%), mp=158°-159°. The mother liquor was evaporated to a crystalline residue which was subjected to an oil pump vacuum. A solution of the residue in a minimum volume of warm dichloromethane was applied to a column (56×3.2 cm) of dry column grade neutral alumina prepacked in toluene. Elution was with toluene (400 ml), toluene-dichloromethane (4:1, 500 ml) followed by dichloromethane. The product was eluted with dichloromethane. The fractionation was monitored by t.l.c. on Alox-25 uv254 plates with dichloromethane-methanol (19:1) as developer. Fractions which contained only product were evaporated to a syrup which crystallized. Recrystallization with decolorization from methanol gave product; wt. 0.93 g (13%), mp=158°-160°. This material, combined with material obtained above, was recrystallized with decolorization from methanol to give pure titled product; wt. 5.46 g, mp=159°-160°.

Workup

  1. custompresaturated at 0°
  2. temperatureheated in a sealed bomb at 100° for 4 days
  3. temperatureThe resulting cooled solution
  4. filtrationwas filtered
  5. customthe filtrate was evaporated to a syrup which
  6. customcrystallized
  7. dissolutionThe residue was dissolved in dichloromethane-methanol
  8. customthe solution was evaporated to a syrup
  9. customCrystallization from methanol
  10. customgave crude titled product
  11. customThe mother liquor was evaporated to a crystalline residue which
  12. washElution
  13. washThe product was eluted with dichloromethane
  14. customwere evaporated to a syrup which
  15. customcrystallized
  16. customRecrystallization with decolorization from methanol
  17. customgave product
  18. customobtained above,
  19. customwas recrystallized with decolorization from methanol

Sources & evidence

ORD record
ord-6d372754d922438499796b96bcfcf4c0
Source dataset
uspto-grants-1990_06
Patent number
US04935515

Reaction notes

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