1-Azabicyclo[2.2.2]oct-4-yl(diphenyl)methanol → 3-{[3-(Diethylamino)phenyl]oxy}propyl-4-[hydroxy(diphenyl)methyl]-1-azoniabicyclo[2.2.2]octane bromide

HRID 1782501Notes

Reaction equation

HRID 1782501 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][CH2:26][O:27][C:28]1[CH:29]=[C:30]([CH:36]=[CH:37][CH:38]=1)[N:31]([CH2:34][CH3:35])[CH2:32][CH3:33]>CC#N>[Br-:23].[CH2:34]([N:31]([CH2:32][CH3:33])[C:30]1[CH:29]=[C:28]([O:27][CH2:26][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:38]=[CH:37][CH:36]=1)[CH3:35]

Participants

4

Reactant 2

HCID 239923851-Azabicyclo[2.2.2]oct-4-yl(diphenyl)methanolHCID 689633743-[(3-bromopropyl)oxy]-N,N-diethylaniline

Product 1

HCID 115343583-{[3-(Diethylamino)phenyl]oxy}propyl-4-[hydroxy(diphenyl)methyl]-1-azoniabicyclo[2.2.2]octane bromideYield 63%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Following the general procedure outlined in Example 3, 1-azabicyclo[2.2.2]oct-4-yl(diphenyl)methanol (0.0257 g, 0.0876 mmol) and 3-[(3-bromopropyl)oxy]-N,N-diethylaniline (0.0314 g, 0.110 mmol) in 2 CH3CN/3 CHCl3 (4.0 mL) were reacted to give the desired product (0.032.0 g, 63.0%). EI-MS m/z 500(M+) Rt (1.58 min).

Workup

  1. customwere reacted

Sources & evidence

ORD record
ord-13a6f94b14c7421494d2718790e0f673
Source dataset
uspto-grants-2009_03
Patent number
US07498440B2

Reaction notes

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