1-(2-Bromo-ethoxymethyl)-4-chlorobenzene → 1-(2-{[(4-Chlorophenyl)methyl]oxy}ethyl)-4-[hydroxy(diphenyl)methyl]-1-azoniabicyclo[2.2.2]octane Bromide

HRID 533871Notes

Reaction equation

HRID 533871 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][CH2:24][CH2:25][O:26][CH2:27][C:28]1[CH:33]=[CH:32][C:31]([Cl:34])=[CH:30][CH:29]=1>CC#N.C(Cl)(Cl)Cl>[Br-:23].[Cl:34][C:31]1[CH:30]=[CH:29][C:28]([CH2:27][O:26][CH2:25][CH2:24][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:33][CH:32]=1

Participants

4

Reactant 2

HCID 136543741-(2-Bromo-ethoxymethyl)-4-chlorobenzeneHCID 239923851-Azabicyclo[2.2.2]oct-4-yl(diphenyl)methanol

Product 1

HCID 116496051-(2-{[(4-Chlorophenyl)methyl]oxy}ethyl)-4-[hydroxy(diphenyl)methyl]-1-azoniabicyclo[2.2.2]octane BromideYield 32%

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-{[(2-bromoethyl)oxy]methyl}-4-chlorobenzene (36 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 (17.4 mg, 32%). LC/MS ESI RT 2.09 min M+462

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-06153f2da5214d7b8be9d84112334e5a
Source dataset
uspto-grants-2014_10
Patent number
US08853404B2

Reaction notes

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