Benzene, ((2-bromoethoxy)methyl)- → 4-[Hydroxy(di-2-naphthalenyl)methyl]-1-{2-[(phenylmethyl)oxy]ethyl}-1-azoniabicyclo[2.2.2]octane bromide

HRID 1782486Notes

Reaction equation

HRID 1782486 reaction equation
[N:1]12[CH2:8][CH2:7][C:4]([C:9]([C:21]3[CH:30]=[CH:29][C:28]4[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=4)[CH:22]=3)([C:11]3[CH:20]=[CH:19][C:18]4[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=4)[CH:12]=3)[OH:10])([CH2:5][CH2:6]1)[CH2:3][CH2:2]2.[C:31]1([CH2:37][O:38][CH2:39][CH2:40][Br:41])[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1>CC#N>[Br-:41].[OH:10][C:9]([C:21]1[CH:30]=[CH:29][C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[CH:22]=1)([C:11]1[CH:20]=[CH:19][C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH:12]=1)[C:4]12[CH2:3][CH2:2][N+:1]([CH2:40][CH2:39][O:38][CH2:37][C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)([CH2:6][CH2:5]1)[CH2:8][CH2:7]2

Participants

4

Reactant 2

HCID 73833Benzene, ((2-bromoethoxy)methyl)-HCID 689619771-Azabicyclo[2.2.2]oct-4-yl(di-2-naphthalenyl)methanol

Product 1

HCID 115053814-[Hydroxy(di-2-naphthalenyl)methyl]-1-{2-[(phenylmethyl)oxy]ethyl}-1-azoniabicyclo[2.2.2]octane bromideYield 25%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Following the general procedure outlined in Example 3, 1-azabicyclo[2.2.2]oct-4-yl(di-2-naphthalenyl)methanol (0.063.7 g, 0.162 mmol) and 2-bromoethyl phenylmethyl ether (0.0384 mL, 0.243 mmol) in 2 CH3CN/3 CHCl3 (4.0 mL) were reacted to give the desired product (0.0246 g, 25.0%). EI-MS m/z 528(M+) Rt (2.36 min).

Workup

  1. customwere reacted

Sources & evidence

ORD record
ord-6f103f309c7840c2a61752374acb7265
Source dataset
uspto-grants-2009_03
Patent number
US07498440B2

Reaction notes

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