(3-Bromopropyl)benzene → 4-[Hydroxy(di-2-thienyl)methyl]-1-(3-phenylpropyl)-1-azoniabicyclo[2.2.2]octane bromide

HRID 533808Notes

Reaction equation

HRID 533808 reaction equation
[N:1]12[CH2:8][CH2:7][C:4]([C:9]([C:16]3[S:17][CH:18]=[CH:19][CH:20]=3)([C:11]3[S:12][CH:13]=[CH:14][CH:15]=3)[OH:10])([CH2:5][CH2:6]1)[CH2:3][CH2:2]2.[Br:21][CH2:22][CH2:23][CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1>C(Cl)(Cl)Cl>[Br-:21].[OH:10][C:9]([C:16]1[S:17][CH:18]=[CH:19][CH:20]=1)([C:11]1[S:12][CH:13]=[CH:14][CH:15]=1)[C:4]12[CH2:5][CH2:6][N+:1]([CH2:22][CH2:23][CH2:24][C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)([CH2:8][CH2:7]1)[CH2:2][CH2:3]2

Participants

4

Reactant 2

HCID 12503(3-Bromopropyl)benzeneHCID 688655991-Azabicyclo[2.2.2]oct-4-yl(di-2-thienyl)methanol

Product 1

HCID 689606014-[Hydroxy(di-2-thienyl)methyl]-1-(3-phenylpropyl)-1-azoniabicyclo[2.2.2]octane bromideYield 62.3%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Following the general procedure outlined in Example 4, 1-azabicyclo[2.2.2]oct-4-yl(di-2-thienyl)methanol (0.0688 g, 0.225 mmol) and (3-bromopropyl)benzene (0.070 mL, 0.460 mmol) in 1MeOH/1 CHCl3 (4.0 mL) were reacted to give the desired product (0.0685 g, 62.3%). EI-MS m/z 424(M+) Rt (1.97 min).

Workup

  1. customwere reacted

Sources & evidence

ORD record
ord-c14f8894895c47fc8448a184991f5a14
Source dataset
uspto-grants-2014_10
Patent number
US08853404B2

Reaction notes

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