Hydrochloric Acid → Ropinirole Hydrochloride

HRID 1436851Notes

Reaction equation

HRID 1436851 reaction equation
OO.[OH-].[Na+].[ClH:5].Cl.[CH2:7]([N:10]([CH2:26][CH2:27][CH3:28])[CH2:11][CH2:12][C:13]1[C:18]([CH2:19][C:20](O)=[O:21])=[C:17]([N+:23]([O-])=O)[CH:16]=[CH:15][CH:14]=1)[CH2:8][CH3:9]>[Pd]>[CH3:9][CH2:8][CH2:7][N:10]([CH2:11][CH2:12][C:13]1[CH:14]=[CH:15][CH:16]=[C:17]2[NH:23][C:20](=[O:21])[CH2:19][C:18]=12)[CH2:26][CH2:27][CH3:28].[ClH:5]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 784Hydrogen PeroxideHCID 14798Sodium HydroxideHCID 135309012-(2-(2-(Dipropylamino)ethyl)-6-nitrophenyl)acetic acid hydrochloride

Product 1

HCID 68727Ropinirole Hydrochloride

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

The process as shown above comprises conversion of 2-methyl-3-nitro phenyl acetic acid (II) with thionyl chloride to 2-Methyl-3-nitro-phenylacetyl chloride (III), which upon reaction with Di-n-propyl amine (DPA) gives 2-Methyl-3-nitro phenyl-N,N-di-n-propyl acetamide (IV) in syrup form. This intermediate (IV) is further reduced with Borane/THF and subsequent treatment with HCl/NaOH to give 2-Methyl-3-nitro phenyl ethyl-N,N-di-n-propyl amine (V). Further, compound (V) is treated with Na metal, Ethanol and diethyl oxalate to obtain Ethyl 6-(2-di-n-propylaminoethyl)-2-nitrophenyl pyruvate (VI), which is further treated with hydrogen peroxide , NaOH and HCl and converted to 6-(2-Di-n-propylaminoethyl)-2-nitro phenyl acetic acid hydrochloride (VII). This intermediate is reduced with palladium/carbon to give Ropinirole hydrochloride (Ia).

Sources & evidence

ORD record
ord-a922503d46cb422cbc0687f7b61b15ba
Source dataset
uspto-grants-2009_11
Patent number
US07619095B2

Reaction notes

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