4-Bromoaniline → N-(4-Bromophenyl)-1-azabicyclo[2.2.2]octane-3-carboxamide Hydrochloride

HRID 722171Notes

Reaction equation

HRID 722171 reaction equation
Cl.[N:2]12[CH2:9][CH2:8][CH:5]([CH2:6][CH2:7]1)[CH:4]([C:10]([Cl:12])=[O:11])[CH2:3]2.[Br:13][C:14]1[CH:20]=[CH:19][C:17]([NH2:18])=[CH:16][CH:15]=1.C(N(CC)C(C)C)(C)C>CN(C=O)C>[ClH:12].[Br:13][C:14]1[CH:20]=[CH:19][C:17]([NH:18][C:10]([CH:4]2[CH:5]3[CH2:8][CH2:9][N:2]([CH2:7][CH2:6]3)[CH2:3]2)=[O:11])=[CH:16][CH:15]=1

Participants

5

Reactant 3

HCID 78074-BromoanilineHCID 81531DiisopropylethylamineHCID 126734373-Quinuclidinecarbonyl chloride Hydrochloride

Product 1

HCID 21883433N-(4-Bromophenyl)-1-azabicyclo[2.2.2]octane-3-carboxamide Hydrochloride

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1.00 g (4.76 mmol) of 3-quinuclidinecarbonyl chloride hydrochloride is added at 0° C. to a solution of 900 mg (5.24 mmol) of 4-bromoaniline and 1.85 g (14.28 mmol) of N,N-diisopropylethylamine in about 10 ml of dry DMF. The mixture is stirred at room temperature overnight. Purification by preparative HPLC is followed by chromatography again on silica gel (mobile phase: dichloromethane/methanol/triethylamine 80:20:2). The product is dissolved in methanol and mixed with 1N HCl in methanol. Finally, the solvent is removed. 0.63 g (31% of theory) of the title compound is obtained. The raw material is employed directly in the next synthesis.

Workup

  1. customPurification by preparative HPLC
  2. dissolutionThe product is dissolved in methanol
  3. additionmixed with 1N HCl in methanol
  4. customFinally, the solvent is removed

Sources & evidence

ORD record
ord-9f4d5a6b4afb456992704462bf22b72b
Source dataset
uspto-grants-2006_11
Patent number
US07138410B2

Reaction notes

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