3-Aminoquinuclidine → N-(1-Azabicyclo[2.2.2]oct-3-yl)-5-bromo-2,4-dimethoxybenzamide Monohydrochloride

HRID 364638Notes

Reaction equation

HRID 364638 reaction equation
[NH2:1][CH:2]1[CH:7]2[CH2:8][CH2:9][N:4]([CH2:5][CH2:6]2)[CH2:3]1.[Br:10][C:11]1[C:12]([O:22][CH3:23])=[CH:13][C:14]([O:20][CH3:21])=[C:15]([CH:19]=1)[C:16]([Cl:18])=[O:17]>O1CCCC1>[ClH:18].[N:4]12[CH2:9][CH2:8][CH:7]([CH2:6][CH2:5]1)[CH:2]([NH:1][C:16](=[O:17])[C:15]1[CH:19]=[C:11]([Br:10])[C:12]([O:22][CH3:23])=[CH:13][C:14]=1[O:20][CH3:21])[CH2:3]2

Participants

4

Reactant 2

HCID 1232383-AminoquinuclidineHCID 135050985-Bromo-2,4-dimethoxybenzoyl chloride

Product 1

HCID 14097661N-(1-Azabicyclo[2.2.2]oct-3-yl)-5-bromo-2,4-dimethoxybenzamide Monohydrochloride

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 3-aminoquinuclidine (1.12 g, 0.0089 mole) in 20 ml tetrahydrofuran was added dropwise to a stirred solution of 5-bromo-2,4-dimethoxybenzoyl chloride (2.50 g, 0.0089 mole) in 100 ml tetrahydrofuran. The mixture was stirred at ambient temperature for 65 hr, and the solid was collected by filtration to yield 2.77 g. Recrystallization from methanol-isopropyl ether gave 1.45 g (40.2%), m.p. 240°-243° C.

Workup

  1. filtrationthe solid was collected by filtration
  2. customto yield 2.77 g
  3. customRecrystallization from methanol-isopropyl ether
  4. customgave 1.45 g (40.2%), m.p. 240°-243° C.

Sources & evidence

ORD record
ord-577738d890e644d6ae6ef2f1a4f9e6fd
Source dataset
uspto-grants-1986_08
Patent number
US04605652

Reaction notes

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