HCID 9879259, compound → HCID 91989402, compound

HRID 1266991Notes

Reaction equation

HRID 1266991 reaction equation
C([N:8]1[CH:13]2[CH2:14][CH2:15][CH:9]1[CH2:10][N:11]([C:16]1[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=1)[CH2:12]2)C1C=CC=CC=1.[ClH:23].CO>>[ClH:23].[F:22][C:19]1[CH:20]=[CH:21][C:16]([N:11]2[CH2:10][CH:9]3[NH:8][CH:13]([CH2:14][CH2:15]3)[CH2:12]2)=[CH:17][CH:18]=1

Participants

3

Reactant 2

HCID 9879259HCID 9879259, compoundHCID 21893726Hydrochloride methanol

Product 1

HCID 91989402HCID 91989402, compoundYield 100%

Procedure

8-Benzyl-3-(4-fluoro-phenyl)-3,8-diaza-bicyclo[3.2.1]octane (2.7 g, 9.11 mmol) was dissolved in 1N hydrochloric acid/methanol (150 mL) and under nitrogen 10% palladium on carbon (1.4 g) was added. The reaction was hydrogenated at 1 atmosphere for 2 hours. The reaction was filtered through Celite and concentrated to yield 3-(4-Fluoro-phenyl)-3,8-diaza-bicyclo[3.2.1]octane, hydrochoride salt (2.2 g, 100%) as a white solid which had the following properties: Mp. 129-131° C.; 1H NMR CDCl3 δ: 9.69 (brd s, 1H), 7.07-6.95 (m, 2H), 6.90-6.80 (m, 2H), 4.05 (brd s, 2H), 3.49 (d, J=10.4 Hz, 2H), 3.08 (d, J=11.2 Hz, 2H), 2.00-1.84 (m, 2H).

Workup

  1. additionwas added
  2. filtrationThe reaction was filtered through Celite
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-10f27155c7db470f835e3d85fdb4776e
Source dataset
uspto-grants-2003_04
Patent number
US06552015B2

Reaction notes

Loading…