2-Benzyl-5-(4-fluorophenyl)-2,5-diazabicyclo[2.2.2]octane → 2-(4-Fluorophenyl)-2,5-diazabicyclo[2.2.2]octane, hydrochoride salt

HRID 1266992Notes

Reaction equation

C([N:8]1[CH2:13][CH:12]2[CH2:14][CH2:15][CH:9]1[CH2:10][N:11]2[C:16]1[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=1)C1C=CC=CC=1.[ClH:23].CO>>[ClH:23].[F:22][C:19]1[CH:18]=[CH:17][C:16]([N:11]2[CH2:10][CH:9]3[CH2:15][CH2:14][CH:12]2[CH2:13][NH:8]3)=[CH:21][CH:20]=1

Participants

Reactant 2

HCID 99008222-Benzyl-5-(4-fluorophenyl)-2,5-diazabicyclo[2.2.2]octane

HCID 21893726Hydrochloride methanol

Product 1

HCID 1317237882-(4-Fluorophenyl)-2,5-diazabicyclo[2.2.2]octane, hydrochoride saltYield 100%

Procedure

2-Benzyl-5-(4-fluoro-phenyl)-2,5-diaza-bicyclo[2.2.2]octane (1.1 g, 3.71 mmol) was dissolved in 1N hydrochloric acid/methanol (60 mL) and under nitrogen 10% palladium on carbon (0.50 g) was added. The reaction was hydrogenated at 1 atmosphere for 2 hours. The reaction was filtered through Celite and concentrated to yield 2-(4-Fluoro-phenyl)-2,5-diaza-bicyclo[2.2.2]octane, hydrochoride salt (0.90 g, 100%) as an off white solid which had the following properties: Mp. 154-156° C.; 1H NMR CDCl3 δ: 9.74 (brd s, 1H), 9.67 (brd s, 1H), 7.00 (t, J=9.1 Hz, 2H), 6.68-6.61 (m, 2H), 4.07 (s, 1H), 3.70 (brd s, 1H), 3.63 (d, J=11.2 Hz, 1H), 3.29 (d, J=10.8 Hz, 1H), 3.23 (brd s, 2H), 2.19-2.04 (m, 1H), 1.95-1.83 (m, 1H), 1.81-1.64 (m, 2H).

Workup

additionwas added
filtrationThe reaction was filtered through Celite
concentrationconcentrated

Sources & evidence

ORD record: ord-61798fe8dc1245bab0f779f399728686
Source dataset: uspto-grants-2003_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06552015B2

Reaction notes

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