Hydrochloric Acid → Atipamezole hydrochloride

HRID 1972139Notes

Reaction equation

HRID 1972139 reaction equation
[ClH:1].Cl.[CH2:3]([C:5]1([C:16]2[N:17]=[CH:18][NH:19][CH:20]=2)[C:13](=O)[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6]1=O)[CH3:4].[H][H]>[Pd]>[ClH:1].[CH2:3]([C:5]1([C:16]2[NH:17][CH:18]=[N:19][CH:20]=2)[CH2:6][C:7]2[C:12](=[CH:11][CH:10]=[CH:9][CH:8]=2)[CH2:13]1)[CH3:4]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 178418361HCID 178418361, compoundHCID 178435263HCID 178435263, compound

Product 1

HCID 13649426Atipamezole hydrochloride

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Conditions

Temperature
82.5 °C

Procedure

Palladium catalyst (1.4 g of 10% Pd/C) was suspended in the hydrochloric acid solution of 2-ethyl-2-(1H-imidazol-4-yl)indan-1,3-dione hydrochloride. The obtained suspension was poured into a hydrogenation autoclave. Hydrogen was supplied to autoclave to 3.0 bar. The reaction mixture was stirred and heated to 80-85° C. The typical hydrogenation time was 6 hours. After hydrogenation the reaction mixture was filtered to remove the catalyst. The filtrate was cooled to (−5)° C., the precipitates were separated by filtration. The obtained crude 5-(2-ethyl-2,3-dihydro-1H-inden-2-yl)-1H-imidazole hydrochloride was dried at 50° C. under reduced pressure. The yield was 3.7 g of a white powder.

Workup

  1. additionThe obtained suspension was poured into a hydrogenation autoclave
  2. filtrationAfter hydrogenation the reaction mixture was filtered
  3. customto remove the catalyst
  4. temperatureThe filtrate was cooled to (−5)° C
  5. custom, the precipitates were separated by filtration

Sources & evidence

ORD record
ord-98531682b95643c484232ad2585ec1e2
Source dataset
uspto-grants-2013_04
Patent number
US08431717B2

Reaction notes

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