Hydrochloric Acid → 3-Methyl-3,9-diazabicyclo[3.3.1]nonane

HRID 1986017Notes

Reaction equation

HRID 1986017 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[CH3:7][N:8]1[C:15](=O)[CH:14]2[NH:17][CH:10]([CH2:11][CH2:12][CH2:13]2)[C:9]1=O.Cl>C1COCC1.CCOCC>[CH3:7][N:8]1[CH2:15][CH:14]2[NH:17][CH:10]([CH2:11][CH2:12][CH2:13]2)[CH2:9]1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 21226445Aluminium lithium hydrideHCID 68843919HCID 68843919, compound

Product 1

HCID 199606393-Methyl-3,9-diazabicyclo[3.3.1]nonane

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolvent2×HCID 8028TetrahydrofuranSolvent2×

Procedure

To a stirred cold (0-5° C.) suspension of LAH (205 mg, 5.40 mmol) in an THF (15 ml) a solution of 3-methyl-3,9-diazabicyclo[3.3.1]nonane-2,4-dione (375 mg) in THF (5 ml) was added and the mixture was heated to reflux for 1-2 h. Rxn was cooled in a ice bath and quenched by addition of water (0.2 ml), 15% NaOH (0.6 ml) and water (0.2 ml) and the suspension was vigorously stirred and filtered and dried over Na2SO4. Evaporation of solvents gave light-brown oil which was dissolved in ether and treated with 1N HCl in ether to afford 3-methyl-3,9-diazabicyclo[3.3.1]nonane and isolated as bis-HCl salt. MS: m/e 141 (MH+). 1H NMR (500 MHz, CD3OD): δ ppm 1.34-1.59 (5H, m), 2.02-2.32 (6H, m), 2.57-2.97 (4H, m).

Workup

  1. additionwas added
  2. temperaturethe mixture was heated
  3. temperatureto reflux for 1-2 h
  4. temperatureRxn was cooled in a ice bath
  5. customquenched by addition of water (0.2 ml), 15% NaOH (0.6 ml) and water (0.2 ml)
  6. filtrationfiltered
  7. dry with materialdried over Na2SO4
  8. customEvaporation of solvents
  9. customgave light-brown oil which

Sources & evidence

ORD record
ord-6cd091c021a94205bb982b9f912eb391
Source dataset
uspto-grants-2009_06
Patent number
US07547690B2

Reaction notes

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