(3R)-N-(4'-Nitrobiphenyl-4-yl)quinuclidine-3-carboxamide hydrochloride → (3R)-N-(4'-Aminobiphenyl-4-yl)quinuclidine-3-carboxamide dihydrochloride

HRID 899174Notes

Reaction equation

HRID 899174 reaction equation
[ClH:1].[N+:2]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[CH:16]=[CH:15][C:14]([NH:17][C:18]([C@@H:20]3[CH:25]4[CH2:26][CH2:27][N:22]([CH2:23][CH2:24]4)[CH2:21]3)=[O:19])=[CH:13][CH:12]=2)=[CH:7][CH:6]=1)([O-])=O>CO.Cl.[Pd]>[ClH:1].[ClH:1].[NH2:2][C:5]1[CH:10]=[CH:9][C:8]([C:11]2[CH:12]=[CH:13][C:14]([NH:17][C:18]([C@@H:20]3[CH:25]4[CH2:24][CH2:23][N:22]([CH2:27][CH2:26]4)[CH2:21]3)=[O:19])=[CH:15][CH:16]=2)=[CH:7][CH:6]=1

Participants

5

Reactant 1

HCID 67427704(3R)-N-(4'-Nitrobiphenyl-4-yl)quinuclidine-3-carboxamide hydrochloride

Product 1

HCID 67427707(3R)-N-(4'-Aminobiphenyl-4-yl)quinuclidine-3-carboxamide dihydrochloride

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 313Hydrochloric AcidSolventHCID 887MethanolSolvent

Procedure

A solution of 739 mg (2.10 mmol) of (3R)-N-(4′-nitrobiphenyl-4-yl)quinuclidine-3-carboxamide (Example 6A) in 10 ml of methanol and 5 ml of 2 N hydrochloric acid is hydrogenated under atmospheric pressure in the presence of 448 mg (0.21 mmol) of 5% palladium on carbon for 2 h. Filtration through kieselgur is followed by washing with methanol and concentration of the filtrate and drying under high vacuum. 755 mg (89.2% of theory) of the title compound are obtained.

Workup

  1. filtrationFiltration through kieselgur
  2. washby washing with methanol and concentration of the filtrate
  3. customdrying under high vacuum

Sources & evidence

ORD record
ord-04ff60f8e6774db49aa8265c816a9ead
Source dataset
uspto-grants-2008_04
Patent number
US07354930B2

Reaction notes

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