Dimethyl Sulfoxide → 1-(4-Carboxymethylbenzyl)-4-aza-1-azoniabicyclo[2.2.2]octane bromide

HRID 348055Notes

Reaction equation

HRID 348055 reaction equation
[Br:1]C[C:3]1[CH:4]=[C:5]([CH2:9][C:10]([OH:12])=[O:11])[CH:6]=[CH:7][CH:8]=1.[N:13]12[CH2:20][CH2:19][N:16]([CH2:17][CH2:18]1)[CH2:15][CH2:14]2.O.[CH3:22]S(C)=O>>[Br-:1].[C:10]([CH2:9][C:5]1[CH:4]=[CH:3][C:8]([CH2:22][N+:13]23[CH2:20][CH2:19][N:16]([CH2:17][CH2:18]2)[CH2:15][CH2:14]3)=[CH:7][CH:6]=1)([OH:12])=[O:11]

Participants

5

Reactant 4

HCID 679Dimethyl Sulfoxide2×HCID 962WaterHCID 9237DabcoHCID 103765092-(3-(Bromomethyl)phenyl)acetic acid

Product 1

HCID 210831751-(4-Carboxymethylbenzyl)-4-aza-1-azoniabicyclo[2.2.2]octane bromide

Procedure

At 70° C., 1.0 g of (3-bromomethylphenyl) acetic acid in 5 ml of dimethyl sulfoxide were added to a solution of 1.5 g of 1,4-diazabicyclo[2.2.2]octane in 10 ml of dimethyl sulfoxide. After 1 h, 100 ml of water were added and the mixture was freeze-dried. The residue was digested with acetone. The residue contained the product of molecular weight 261.35 (cation: C15H21N2O2+); MS (ESI) 261.1 (M+).

Workup

  1. customthe mixture was freeze-dried

Sources & evidence

ORD record
ord-330392bcefb54e11ac8ed2bfdedcc4d3
Source dataset
uspto-grants-2007_02
Patent number
US07176194B2

Reaction notes

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