Phenethyl bromide → 4-[Hydroxy(diphenyl)methyl]-1-(2-phenylethyl)-1-azoniabicyclo[2.2.2]octane Bromide

HRID 1875577Notes

Reaction equation

HRID 1875577 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][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1>CC#N.C(Cl)Cl.CO.CS(C)=O>[Br-:23].[OH:10][C:9]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)([C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1)[C:4]12[CH2:5][CH2:6][N+:1]([CH2:24][CH2:25][C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)([CH2:2][CH2:3]1)[CH2:8][CH2:7]2

Participants

5

Reactant 2

HCID 7666Phenethyl bromideHCID 239923851-Azabicyclo[2.2.2]oct-4-yl(diphenyl)methanol

Product 1

HCID 116914704-[Hydroxy(diphenyl)methyl]-1-(2-phenylethyl)-1-azoniabicyclo[2.2.2]octane BromideYield 48.6%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 22226298MeOH ACN DCMSolvent

Procedure

To a solution of 1-azabicyclo[2.2.2]oct-4-yl(diphenyl)methanol (0.0775 g, 0.264 mmol) in CH3CN/DCM/MeOH (2 mL/2 mL/1 mL) was added (2-bromoethyl)benzene (0.38 mL, 2.78 mmol). The solution was allowed to stir at room temperature for 4 days and then concentrated under vacuum to give a white solid. This residue was dissolved in DMSO and purified by preparatory HPLC to give the title compound (0.0612 g, 48.6%). ELMS m/z 398 (M+) Rt (2.06 min).

Workup

  1. concentrationconcentrated under vacuum
  2. customto give a white solid
  3. custompurified by preparatory HPLC

Sources & evidence

ORD record
ord-2b06f11ec981423cb8729de845da3038
Source dataset
uspto-grants-2012_11
Patent number
US08309572B2

Reaction notes

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