1-(3-Bromopropoxy)-3-nitrobenzene → 4-[Hydroxy(diphenyl)methyl]-1-{3-[(3-nitrophenyl)oxy]propyl}-1-azoniabicyclo[2.2.2]octane bromide

HRID 2283103Notes

Reaction equation

HRID 2283103 reaction equation
[N:1]12[CH2:8][CH2:7][C:4]([C:9]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)[OH:10])([CH2:5][CH2:6]1)[CH2:3][CH2:2]2.[N+:23]([C:26]1[CH:27]=[C:28]([O:32][CH2:33][CH2:34][CH2:35][Br:36])[CH:29]=[CH:30][CH:31]=1)([O-:25])=[O:24]>CC#N>[Br-:36].[OH:10][C:9]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)([C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1)[C:4]12[CH2:5][CH2:6][N+:1]([CH2:35][CH2:34][CH2:33][O:32][C:28]3[CH:29]=[CH:30][CH:31]=[C:26]([N+:23]([O-:25])=[O:24])[CH:27]=3)([CH2:2][CH2:3]1)[CH2:8][CH2:7]2

Participants

4

Reactant 2

HCID 71723011-(3-Bromopropoxy)-3-nitrobenzeneHCID 239923851-Azabicyclo[2.2.2]oct-4-yl(diphenyl)methanol

Product 1

HCID 115703064-[Hydroxy(diphenyl)methyl]-1-{3-[(3-nitrophenyl)oxy]propyl}-1-azoniabicyclo[2.2.2]octane bromideYield 82.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Following the general procedure outlined in Example 3, 1-azabicyclo[2.2.2]oct-4-yl(diphenyl)methanol (0.0608 g, 0.207 mmol) and 3-bromopropyl 3-nitrophenyl ether (0.0730 g, 0.281 mmol) in 2 CH3CN/3 CHCl3 (4.0 mL) were reacted to give the desired product (0.0942 g, 82.2%). EI-MS m/z 474 (M+) Rt (2.04 min).

Workup

  1. customwere reacted

Sources & evidence

ORD record
ord-a506be1590a64408bf944b7e3a2559a2
Source dataset
uspto-grants-2015_09
Patent number
US09144571B2

Reaction notes

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