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

HRID 1606920Notes

Reaction equation

HRID 1606920 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-b5adc83d84674b8a9545c5a4029338ae
Source dataset
uspto-grants-1989_09
Patent number
US04863919

Reaction notes

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