Acetonitrile → 4-[Hydroxy(diphenyl)methyl]-1-(2-phenylethyl)-1-azoniabicyclo[2.2.1]heptane bromide

HRID 499659Notes

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.CC#N.[Br:25][CH2:26][CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1>C(OCC)(=O)C>[Br-:25].[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]([CH2:26][CH2:27][C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=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 (30.5 mg, 0.109 mmol) in 2 CH3CN/3 CHCl3 (2.5 mL) was added (2-bromoethyl)benzene (0.03 mL, 0.22 mmol). The solution was stirred at 60° C. for 16 h. The reaction was cooled down to room temperature. Trituration with ethyl acetate caused a solid to crash out of solution. This solid was filtered off, and washed with ethyl acetate to give the title compound (36.4 mg, 72%). EI-MS m/z 384 (M+) Rt (1.87 min).

Workup

temperatureThe reaction was cooled down to room temperature
filtrationThis solid was filtered off
washwashed with ethyl acetate

Sources & evidence

ORD record: ord-442296c6bb92420f84d2f9cf421a6134
Source dataset: uspto-grants-2010_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07767691B2

Reaction notes

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