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

HRID 2167572Notes

Reaction equation

HRID 2167572 reaction equation
[N:1]12[CH2:8][CH2:7][C:4]([C:9]([C:18]3[CH:23]=[CH:22][C:21]([F:24])=[CH:20][CH:19]=3)([C:11]3[CH:16]=[CH:15][C:14]([F:17])=[CH:13][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:14]1[CH:15]=[CH:16][C:11]([C:9]([C:18]2[CH:19]=[CH:20][C:21]([F:24])=[CH:22][CH:23]=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:12][CH:13]=1

Participants

4

Reactant 2

HCID 73833Benzene, ((2-bromoethoxy)methyl)-HCID 689591291-Azabicyclo[2.2.2]oct-4-yl[bis(4-fluorophenyl)]methanol

Product 1

HCID 115920044-[Bis(4-fluorophenyl)(hydroxy)methyl]-1-{2-[(phenylmethyl)oxy]ethyl}-1-azoniabicyclo[2.2.2]octane bromideYield 66.3%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Following the general procedure outlined in Example 3, 1-azabicyclo[2.2.2]oct-4-yl[bis(4-fluorophenyl)]methanol (0.0489 g, 0.148 mmol) and 2-bromoethyl phenylmethyl ether (0.0352 mL, 0.222 mmol) in 2 CH3CN/3 CHCl3 (4.0 mL) were reacted to give the desired product (0.0534 g, 66.1%). EI-MS m/z 464 (M+) Rt (1.99 min).

Workup

  1. customwere reacted

Sources & evidence

ORD record
ord-0f222b95524b421daef5682055cbead4
Source dataset
uspto-grants-2015_06
Patent number
US09045469B2

Reaction notes

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