Benzene, ((2-bromoethoxy)methyl)- → 4-(Hydroxy{bis[3-(methyloxy)phenyl]}methyl)-1-{2-[(phenylmethyl)oxy]ethyl}-1-azoniabicyclo[2.2.2]octane Bromide

HRID 1782476Notes

Reaction equation

HRID 1782476 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([CH2:33][O: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][O:34][CH2:33][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 73833Benzene, ((2-bromoethoxy)methyl)-HCID 689576291-Azabicyclo[2.2.2]oct-4-yl{bis[3-(methyloxy)phenyl]}methanol

Product 1

HCID 116641524-(Hydroxy{bis[3-(methyloxy)phenyl]}methyl)-1-{2-[(phenylmethyl)oxy]ethyl}-1-azoniabicyclo[2.2.2]octane BromideYield 33.8%

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 (0.0538 g, 0.152 mmol) and 2-bromoethyl phenylmethyl ether (0.0361 mL, 0.228 mmol) in 2 CH3CN/3 CHCl3 (4.0 mL) were reacted to give the desired product (0.0292 g, 33.8%). EI-MS m/z 488(M+) Rt (2.03 min).

Workup

  1. customwere reacted

Sources & evidence

ORD record
ord-4da0403fa7f14fb6b2ef8fd5288bd592
Source dataset
uspto-grants-2009_03
Patent number
US07498440B2

Reaction notes

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