Hydrochloric Acid → 1,5-Diazabicyclo(4.3.0)nonane

HRID 888761Notes

Reaction equation

HRID 888761 reaction equation
O1CCO[CH:2]1[CH2:6][CH2:7][CH2:8][NH:9][CH:10](C)[CH2:11][CH2:12][NH2:13].Cl.[OH-].[Na+]>O>[N:9]12[CH2:2][CH2:6][CH2:7][CH:8]1[NH:13][CH2:12][CH2:11][CH2:10]2

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 688622203-(3-([1,3]Dioxolan-2-yl)propylamino)-1-aminobutane

Product 1

HCID 110946241,5-Diazabicyclo(4.3.0)nonaneYield 62.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

In a 500 ml three-necked flask, 41.08 g (0.2 mol) of 3-{3-([1,3]dioxolan-2-yl)propylamino}-1-aminobutane are added to 65 g of 33% strength hydrochloric acid and 100 ml of water and the mixture is stirred vigorously for three hours. It is then neutralized by dropwise addition of 100 ml of 30% strength sodium hydroxide solution, and the neutralized solution is subjected to extraction with CH2Cl2. The organic extracts are dried over sodium carbonate and concentrated. This gives 27.54 g of a reddish liquid. Distillation under a high vacuum (overhead temperature=34° C., p=0.006 mbar) gives 15.87 g of 1,5-diazabicyclo[4.3.0]nonane as a colourless oil.

Workup

  1. extractionthe neutralized solution is subjected to extraction with CH2Cl2
  2. dry with materialThe organic extracts are dried over sodium carbonate
  3. concentrationconcentrated
  4. distillationDistillation under a high vacuum (overhead temperature=34° C., p=0.006 mbar)

Sources & evidence

ORD record
ord-a6f3f587c63e41c8895566b2010ee379
Source dataset
uspto-grants-2012_08
Patent number
US08252784B2

Reaction notes

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