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

HRID 499682Notes

Reaction equation

HRID 499682 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][CH:30]=[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 68522Benzene, (3-bromopropoxy)-HCID 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 73.7%

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 (0.2 mg, 0.7 mmol) and 3-bromopropylphenyl-ether (0.17 mL, 1.1 mmol) in 2 CH3CN/3 CHCl3 (15 mL) were reacted to give the desired product (255 mg, 64%). 1H NMR (400 MHz, CD3OD) δ 7.5 (m, 4H), 7.35 (m, 3H), 7.3-7.2 (m, 4H), 6.9 (m, 4H), 4.07 (m, 3H), 3.8-3.7 (m, 2H), 3.62 (m, 5H), 3.6-2.5 (m, 2H), 2.4-2.3 (m, 2H), 2.3-2.1 (m, 51).

Workup

  1. customwere reacted

Sources & evidence

ORD record
ord-c878385de2a047138aa7065792c7d276
Source dataset
uspto-grants-2010_08
Patent number
US07767691B2

Reaction notes

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