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 1860380Notes

Reaction equation

HRID 1860380 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>[Pd]>[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

4

Reactant 2

HCID 99008222-Benzyl-5-(4-fluorophenyl)-2,5-diazabicyclo[2.2.2]octaneHCID 21893726Hydrochloride methanol

Product 1

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

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

2-Benzyl-5-(4-fluorophenyl)-2,5-diazabicyclo[2.2.2]octane (1.1 g, 3.71 mmol) was dissolved in 1N hydrochloric acid/methanol (60 mL); 10% palladium on carbon (0.50 g) was then added under nitrogen. A hydrogenation was then carried out at 1 atmosphere for 2 hours. The reaction mixture was then filtered through Celite and concentrated to yield 2-(4-fluorophenyl)-2,5-diazabicyclo[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

  1. filtrationThe reaction mixture was then filtered through Celite
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-836f72fbb00448f594ccb8b8985e027e
Source dataset
uspto-grants-2003_03
Patent number
US06531468B2

Reaction notes

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