Benzene, (3-bromopropoxy)- → 4-(Hydroxy{bis[3-(methyloxy)phenyl]}methyl)-1-[3-(phenyloxy)propyl]-1-azoniabicyclo[2.2.2]octane bromide

HRID 1875629Notes

Reaction equation

HRID 1875629 reaction equation
[N:1]12[CH2:8][CH2:7][C:4]([C:9]([C:19]3[CH:24]=[CH:23][CH:22]=[C:21]([O:25][CH3:26])[CH:20]=3)([C:11]3[CH:16]=[CH:15][CH:14]=[C:13]([O:17][CH3:18])[CH:12]=3)[OH:10])([CH2:5][CH2:6]1)[CH2:3][CH2:2]2.[C:27]1([O:33][CH2:34][CH2:35][CH2:36][Br:37])[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1>CC#N>[Br-:37].[OH:10][C:9]([C:19]1[CH:24]=[CH:23][CH:22]=[C:21]([O:25][CH3:26])[CH:20]=1)([C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([O:17][CH3:18])[CH:12]=1)[C:4]12[CH2:5][CH2:6][N+:1]([CH2:36][CH2:35][CH2:34][O:33][C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)([CH2:2][CH2:3]1)[CH2:8][CH2:7]2

Participants

4

Reactant 2

HCID 68522Benzene, (3-bromopropoxy)-HCID 689576291-Azabicyclo[2.2.2]oct-4-yl{bis[3-(methyloxy)phenyl]}methanol

Product 1

HCID 117068174-(Hydroxy{bis[3-(methyloxy)phenyl]}methyl)-1-[3-(phenyloxy)propyl]-1-azoniabicyclo[2.2.2]octane bromideYield 33.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Following the general procedure outlined in Example 3, 1-azabicyclo[2.2.2]oct-4-yl{bis[3-(methyloxy)phenyl]}methanol (0.0506 g, 0.143 mmol) and 3-bromopropyl phenyl ether (0.0338 mL, 0.214 mmol) in 2 CH3CN/3 CHCl3 (4.0 mL) were reacted to give the desired product (0.027 g, 33.2%). EI-MS m/z 488 (M+) Rt (2.02 min).

Workup

  1. customwere reacted

Sources & evidence

ORD record
ord-ecc8e8c179bb48729fff4aeae2dc0172
Source dataset
uspto-grants-2012_11
Patent number
US08309572B2

Reaction notes

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