((4-Bromobutoxy)methyl)benzene → 4-[Hydroxy(diphenyl)methyl]-1-{4-[(phenylmethyl)oxy]butyl}-1-azoniabicyclo[2.2.1]heptane bromide

HRID 499668Notes

Reaction equation

HRID 499668 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.[C:22]1([CH2:28][O:29][CH2:30][CH2:31][CH2:32][CH2:33][Br:34])[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>CC#N>[Br-:34].[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]([CH2:33][CH2:32][CH2:31][CH2:30][O:29][CH2:28][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)([CH2:6][CH2:5]1)[CH2:2][CH2:3]2

Participants

4

Reactant 2

HCID 4422181((4-Bromobutoxy)methyl)benzeneHCID 426258561-Azabicyclo[2.2.1]hept-4-yl(diphenyl)methanol

Product 1

HCID 160415844-[Hydroxy(diphenyl)methyl]-1-{4-[(phenylmethyl)oxy]butyl}-1-azoniabicyclo[2.2.1]heptane bromideYield 7.3%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Following the general procedure outlined in Example 1, 1-azabicyclo[2.2.1]hept-4-yl(diphenyl)methanol (33.1 mg, 0.118 mmol) and 4-bromobutyl phenylmethyl ether (0.04 mL, 0.21 mmol) in 2 CH3CN/3 CHCl3 (2.5 mL) were reacted to give the desired product (4.5 mg, 7%). EI-MS m/z 442 (M+) Rt (2.01 min).

Workup

  1. customwere reacted

Sources & evidence

ORD record
ord-eed1111b7fe0426fa3d9aed88873e94d
Source dataset
uspto-grants-2010_08
Patent number
US07767691B2

Reaction notes

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