(1R,4R)-6-benzyl-3,6-diazabicyclo[2.2.1]heptane dihydrobromide → Heptane, Dihydrobromide

HRID 1089229Notes

Reaction equation

HRID 1089229 reaction equation
[BrH:1].Br.[C:3]1([CH2:9]N2C[C@H]3C[C@@H]2CN3)[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1>O.[Pd]>[BrH:1].[BrH:1].[CH3:9][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8]

Participants

4

Reactant 1

HCID 14612541(1R,4R)-6-benzyl-3,6-diazabicyclo[2.2.1]heptane dihydrobromide

Product 1

HCID 21610488Heptane, DihydrobromideYield 180.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 962WaterSolvent

Procedure

A suspension of 76 g (0.217 moles) of (1R, 4R)-5-phenylmethyl-2,5-diazabicyclo-[2.2.1]-heptane, dihydrobromide (9) and 37 g of 10% Pd on C in 1.2 L of water was hydrogenated at atmospheric pressure at 40° C. The reaction was completed within 8 hours. The catalyst was filtered off and the filtrate was evaporated under reduced pressure. The residue was taken up with ethanol and the resulting precipitate was filtered to give 51.4 g (91%) of the titled compound. M.P.=285°. [α]D =-19.83 (c=1.2, 0.1N HCL).

Workup

  1. customwas hydrogenated at atmospheric pressure at 40° C
  2. filtrationThe catalyst was filtered off
  3. customthe filtrate was evaporated under reduced pressure
  4. filtrationthe resulting precipitate was filtered

Sources & evidence

ORD record
ord-1457932d84534b60be11fe19f33ed4fb
Source dataset
uspto-grants-1990_10
Patent number
US04965273

Reaction notes

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