1-Bromo-4-(3-bromopropoxy)benzene → 4-[Hydroxy(diphenyl)methyl]-1-[3-(phenyloxy)propyl]-1-azoniabicyclo[2.2.1]heptane bromide

HRID 499673Notes

Reaction equation

HRID 499673 reaction equation
[N:1]12[CH2:7][C:4]([C:8]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)([C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=3)[OH:9])([CH2:5][CH2:6]1)[CH2:3][CH2:2]2.[Br:22][CH2:23][CH2:24][CH2:25][O:26][C:27]1[CH:32]=[CH:31][C:30](Br)=[CH:29][CH:28]=1>CC#N>[Br-:22].[OH:9][C:8]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[C:4]12[CH2:7][N+:1]([CH2:23][CH2:24][CH2:25][O:26][C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)([CH2:6][CH2:5]1)[CH2:2][CH2:3]2

Participants

4

Reactant 2

HCID 3479241-Bromo-4-(3-bromopropoxy)benzeneHCID 426258561-Azabicyclo[2.2.1]hept-4-yl(diphenyl)methanol

Product 1

HCID 160419344-[Hydroxy(diphenyl)methyl]-1-[3-(phenyloxy)propyl]-1-azoniabicyclo[2.2.1]heptane bromideYield 63.9%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Following the general procedure outlined in Example 2, 1-azabicyclo[2.2.1]hept-4-yl(diphenyl)methanol (31.5 mg, 0.113 mmol) and 4-bromophenyl 3-bromopropyl ether (46.1 mg, 0.157 mmol) in 2 CH3CN/3 CHCl3 (2.5 mL) were reacted to give the desired product (35.7 mg, 55%). EI-MS m/z 492 (M+) Rt (1.94 min).

Workup

  1. customwere reacted

Sources & evidence

ORD record
ord-e8b66fa3a14b4dedb2898bc1da87ec2e
Source dataset
uspto-grants-2010_08
Patent number
US07767691B2

Reaction notes

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