1-Bromo-4-((2-bromoethoxy)methyl)benzene → 1-(2-{[(4-Bromophenyl)methyl]oxy}ethyl)-4-[hydroxy(diphenyl)methyl]-1-azoniabicyclo[2.2.2]octane Bromide

HRID 533874Notes

Reaction equation

HRID 533874 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.[Br:23][C:24]1[CH:29]=[CH:28][C:27]([CH2:30][O:31][CH2:32][CH2:33]Br)=[CH:26][CH:25]=1>CC#N.C(Cl)(Cl)Cl>[Br-:23].[Br:23][C:24]1[CH:25]=[CH:26][C:27]([CH2:30][O: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:28][CH:29]=1

Participants

4

Reactant 2

HCID 136543811-Bromo-4-((2-bromoethoxy)methyl)benzeneHCID 239923851-Azabicyclo[2.2.2]oct-4-yl(diphenyl)methanol

Product 1

HCID 115851161-(2-{[(4-Bromophenyl)methyl]oxy}ethyl)-4-[hydroxy(diphenyl)methyl]-1-azoniabicyclo[2.2.2]octane BromideYield 46.2%

Reagents, catalysts & solvents 1

HCID 22555007Acetonitrile chloroformSolvent

Conditions

Temperature
60 °C

Procedure

1-Azabicyclo[2.2.2]oct-4-yl(diphenyl)methanol (30 mg, 0.102 mmol) was added to a solution of 1-bromo-4-{[(2-bromoethyl)oxy]methyl}benzene (42 mg, 0.143 mmol) in 2:3 CH3CN/CHCl3 (3 mL), and the reaction was heated at 60° C. for 96 h. The reaction was concentrated, and the crude product was washed with EtOAc (3×1 mL). The product was dried under high vacuum to give the title compound (19.4 mg, 32%). LC/MS ESI RT 2.07 min M+506

Workup

  1. concentrationThe reaction was concentrated
  2. washthe crude product was washed with EtOAc (3×1 mL)
  3. customThe product was dried under high vacuum

Sources & evidence

ORD record
ord-bf5627c08f3349728c2139aba0d22497
Source dataset
uspto-grants-2014_10
Patent number
US08853404B2

Reaction notes

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