Benzene, ((2-bromoethoxy)methyl)- → 4-[Hydroxy(diphenyl)methyl]-1-{2-[(phenylmethyl)oxy]ethyl}-1-azoniabicyclo[2.2.1]heptane Bromide

HRID 499658Notes

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][Br:32])[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>CC#N>[Br-:32].[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]([CH2:31][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

Conditions

Temperature: 60 °C

Procedure

To a solution of 1-azabicyclo[2.2.1]hept-4-yl(diphenyl)methanol (50 mg, 0.18 mmol) in 2 CH3CN/3 CHCl3 (4 mL) was added 2-bromoethyl phenylmethyl ether (0.04 mL, 0.25 mmol). The solution was heated at 60° C. for 16 h, cooled down to room temperature and the solvents evaporated under vacuum. The residue was taken up in 2.5 mL of DMSO and purified by preparatory HPLC (without TFA) to give the title compound (32 mg, 36%). EI-MS m/z 414 (M+) Rt (1.92 min).

Workup

temperaturecooled down to room temperature
customthe solvents evaporated under vacuum
custompurified by preparatory HPLC (without TFA)

Sources & evidence

ORD record: ord-af1d8c1eb0064d1d81bc9aa83f1fffaa
Source dataset: uspto-grants-2010_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07767691B2

Reaction notes

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