Hydrochloric Acid → 1,4-Diazabicyclo[3.2.1]octane dihydrochloride

HRID 2117257Notes

Reaction equation

HRID 2117257 reaction equation
C([N:8]1[CH:14]2[CH2:15][N:11]([CH2:12][CH2:13]2)[CH2:10][CH2:9]1)C1C=CC=CC=1.[ClH:16]>[Pd].CCO>[ClH:16].[ClH:16].[N:11]12[CH2:15][CH:14]([CH2:13][CH2:12]1)[NH:8][CH2:9][CH2:10]2

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 598156164-Benzyl-1,4-diazabicyclo[3.2.1]octane

Product 1

HCID 123740781,4-Diazabicyclo[3.2.1]octane dihydrochlorideYield 80%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of 4-benzyl-1,4-diaza-bicyclo[3.2.1]octane (7.5 g, 37 mmol), 5% palladium on carbon (0.75 g, wet), concentrated HCl (7.5 mL) in EtOH (150 mL) was shaken under hydrogen (50 psi) for a period of 20 h at RT. The product precipitated out of the mixture and water was added in order to dissolve the product. The mixture was filtered through a pad of celite and washed with EtOH. The filtrate was concentrated in vacuo to a solid that was azeotroped with EtOH (3×50 mL). The resulting solid was triturated with hot isopropanol and stirred 18 h at RT. The resulting solid was collected by filtration giving 5.6 g (80%) of the title compound: 1H NMR (d6-DMSO, 400 MHz) δ 4.26 (br s, 1H), 3.72 (d, 1H, J=12 Hz), 3.60-3.53 (m, 1H), 3.48-3.35 (m, 7H), 2.33-2.27 (m, 2H); GCMS m/z 112

Workup

  1. customThe product precipitated out of the mixture and water
  2. additionwas added in order
  3. dissolutionto dissolve the product
  4. filtrationThe mixture was filtered through a pad of celite
  5. washwashed with EtOH
  6. concentrationThe filtrate was concentrated in vacuo to a solid
  7. customthat was azeotroped with EtOH (3×50 mL)
  8. customThe resulting solid was triturated with hot isopropanol
  9. stirringstirred 18 h at RT
  10. filtrationThe resulting solid was collected by filtration

Sources & evidence

ORD record
ord-2c93003702944a8ebd6b0237f38958bd
Source dataset
uspto-grants-2008_10
Patent number
US07442694B2

Reaction notes

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