1-(3-Bromopropoxy)-3-chlorobenzene → 1-{3-[(3-Chlorophenyl)oxy]propyl}-4-[hydroxy(diphenyl)methyl]-1-azoniabicyclo[2.2.2]octane bromide

HRID 533818Notes

Reaction equation

HRID 533818 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.[Cl:23][C:24]1[CH:25]=[C:26]([O:30][CH2:31][CH2:32][CH2:33][Br:34])[CH:27]=[CH:28][CH:29]=1>CC#N>[Br-:34].[Cl:23][C:24]1[CH:25]=[C:26]([O:30][CH2:31][CH2:32][CH2:33][N+:1]23[CH2:6][CH2:5][C:4]([C:9]([OH:10])([C:17]4[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=4)[C:11]4[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=4)([CH2:3][CH2:2]2)[CH2:7][CH2:8]3)[CH:27]=[CH:28][CH:29]=1

Participants

4

Reactant 2

HCID 27349291-(3-Bromopropoxy)-3-chlorobenzeneHCID 239923851-Azabicyclo[2.2.2]oct-4-yl(diphenyl)methanol

Product 1

HCID 116135941-{3-[(3-Chlorophenyl)oxy]propyl}-4-[hydroxy(diphenyl)methyl]-1-azoniabicyclo[2.2.2]octane bromideYield 74.4%

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 (0.0479 g, 0.163 mmol) and 3-bromopropyl 3-chlorophenyl ether (0.0552 g, 0.221 mmol) in 2 CH3CN/3 CHCl3 (4.0 mL) were reacted to give the desired product (0.0655 g, 74.4%). EI-MS m/z 462(M+) Rt (2.17 min).

Workup

  1. customwere reacted

Sources & evidence

ORD record
ord-05353052bcba4fb9af20e6e31939981e
Source dataset
uspto-grants-2014_10
Patent number
US08853404B2

Reaction notes

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