Benzene, ((2-bromoethoxy)methyl)- → 4-[Bis(3-fluorophenyl)(hydroxy)methyl]-1-{2-[(phenylmethyl)oxy]ethyl}-1-azoniabicyclo[2.2.2]octane bromide

HRID 533836Notes

Reaction equation

HRID 533836 reaction equation
[N:1]12[CH2:8][CH2:7][C:4]([C:9]([C:18]3[CH:23]=[CH:22][CH:21]=[C:20]([F:24])[CH:19]=3)([C:11]3[CH:16]=[CH:15][CH:14]=[C:13]([F:17])[CH:12]=3)[OH:10])([CH2:5][CH2:6]1)[CH2:3][CH2:2]2.[C:25]1([CH2:31][O:32][CH2:33][CH2:34][Br:35])[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1>CC#N>[Br-:35].[F:17][C:13]1[CH:12]=[C:11]([C:9]([C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([F:24])[CH:19]=2)([OH:10])[C:4]23[CH2:5][CH2:6][N+:1]([CH2:34][CH2:33][O:32][CH2:31][C:25]4[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=4)([CH2:2][CH2:3]2)[CH2:8][CH2:7]3)[CH:16]=[CH:15][CH:14]=1

Participants

4

Reactant 2

HCID 73833Benzene, ((2-bromoethoxy)methyl)-HCID 689587571-Azabicyclo[2.2.2]oct-4-yl[bis(3-fluorophenyl)]methanol

Product 1

HCID 116424064-[Bis(3-fluorophenyl)(hydroxy)methyl]-1-{2-[(phenylmethyl)oxy]ethyl}-1-azoniabicyclo[2.2.2]octane bromideYield 43.2%

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-fluorophenyl)]methanol (0.0507 g, 0.154 mmol) and 2-bromoethyl phenylmethyl ether (0.0365 mL, 0.230 mmol) in 2 CH3CN/3 CHCl3 (4.0 mL) were reacted to give the desired product (0.0362 g, 43.2%). EI-MS m/z 464(M+) Rt (2.02 min).

Workup

  1. customwere reacted

Sources & evidence

ORD record
ord-1de442c53f6f44df88d27c9269776a5b
Source dataset
uspto-grants-2014_10
Patent number
US08853404B2

Reaction notes

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