Hydrochloric Acid → HCID 178435256, compound

HRID 1988810Notes

Reaction equation

HRID 1988810 reaction equation
[CH2:1]([C:3]1([C:13]2[N:14]=[CH:15][NH:16][CH:17]=2)[CH2:11][C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]1O)[CH3:2].O.[ClH:19].[H][H]>[Pd].C(O)C>[ClH:19].[CH2:1]([C:3]1([C:13]2[N:14]=[CH:15][NH:16][CH:17]=2)[CH2:11][C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4]1)[CH3:2]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 178418361HCID 178418361, compoundHCID 178435258HCID 178435258, compound

Product 1

HCID 178435256HCID 178435256, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Conditions

Temperature
0 °C

Procedure

4-(2-ethyl-2,3-dihydro-1-hydroxy-1H-inden-2-yl)-1H-imidazole (5 kg), water (40 kg), 30% HCl (34 kg), ethanol (22 kg) and 10% palladium on charcoal (0.5 kg) are charged. The mixture is stirred under 2.2 bar overpressure of hydrogen at 80±3° C. for 12 hours. The reaction mixture is filtered at 73±2° C., the filter cake is washed with water (7 kg) and the filtrates are combined. The reaction mixture is heated to boil and 50 l of the solvent is distilled off. The solution is cooled to 0±2° C. during 2 h. The solution is seeded during the cooling procedure with atipamezole HCl at 100±5° C., 90±5° C., 80±5° C. and at 70±5° C., until the crystallization starts. The mixture is agitated for two hours at 0±2° C. The crystalline compound is recovered by centrifugation and washed with HCl-water mixture (0.34 kg HCl and 10 kg of water) and then with 18 kg of acetone. The product is dried under reduced pressure raising the temperature gradually to 85±3° C. The yield is 4.8 kg (89%).

Workup

  1. filtrationThe reaction mixture is filtered at 73±2° C.
  2. washthe filter cake is washed with water (7 kg)
  3. temperatureThe reaction mixture is heated
  4. distillation50 l of the solvent is distilled off
  5. customThe solution is seeded during the cooling procedure with atipamezole HCl at 100±5° C., 90±5° C., 80±5° C. and at 70±5° C., until the crystallization
  6. customThe crystalline compound is recovered by centrifugation
  7. washwashed with HCl-water mixture (0.34 kg HCl and 10 kg of water)
  8. customThe product is dried under reduced pressure
  9. temperatureraising the temperature gradually to 85±3° C

Sources & evidence

ORD record
ord-305b55e73b5e497aa72783b01948fedd
Source dataset
uspto-grants-2010_01
Patent number
US07642279B2

Reaction notes

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