6,8-Bis(phenylmethyl)-6,8-diazabicyclo[3.2.2]nonane dihydrochloride → 6,8-Diazabicyclo[3.2.2]nonane 2hcl

HRID 981736Notes

Reaction equation

HRID 981736 reaction equation
[ClH:1].Cl.C1(C[N:10]2[CH2:16][CH:15]3[N:17](CC4C=CC=CC=4)[CH2:18][CH:11]2[CH2:12][CH2:13][CH2:14]3)C=CC=CC=1>[Pd].CO.O>[ClH:1].[ClH:1].[CH:15]12[NH:17][CH2:18][CH:11]([NH:10][CH2:16]1)[CH2:12][CH2:13][CH2:14]2

Participants

4

Reactant 1

HCID 147746376,8-Bis(phenylmethyl)-6,8-diazabicyclo[3.2.2]nonane dihydrochloride

Product 1

HCID 703770826,8-Diazabicyclo[3.2.2]nonane 2hclYield 184.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 22242641Methanol--water (1/1)Solvent

Procedure

A solution of 20.28 g (53.5 mmol) of 6,8-bis(phenylmethyl)-6,8-diazabicyclo[3.2.2]nonane dihydrochloride in 400 of 2:1 methanol-water was hydrogenated using 2.5 g of 20% Pd/C catalyst. The reaction mixture was filtered and evaporated to dryness. The residue was triturated with 2-propanol and filtered to give 9.84 g of 6,8-diazabicyclo[3.2.2]nonane, dihydrochloride, mp 300°-310° dec (92%).

Workup

  1. filtrationThe reaction mixture was filtered
  2. customevaporated to dryness
  3. customThe residue was triturated with 2-propanol
  4. filtrationfiltered

Sources & evidence

ORD record
ord-63bfbf64bc2c46daae1cac1bb90f78a1
Source dataset
uspto-grants-1991_02
Patent number
US04992546

Reaction notes

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