1,4-Dioxane hydrochloride → n,n-Dipropylpropane-1,3-diamine

HRID 348603Notes

Reaction equation

HRID 348603 reaction equation
[CH2:1]([N:4]([CH2:16][CH2:17][CH3:18])[CH2:5][CH2:6][CH2:7][NH:8]C(OC(C)(C)C)=O)[CH2:2][CH3:3].Cl.O1CCOCC1>CO>[CH2:16]([N:4]([CH2:1][CH2:2][CH3:3])[CH2:5][CH2:6][CH2:7][NH2:8])[CH2:17][CH3:18]

Participants

4

Reactant 2

HCID 204431481,4-Dioxane hydrochlorideHCID 23079224N,N-dipropyl-N'-Boc-1,3-propanediamine

Product 1

HCID 239005n,n-Dipropylpropane-1,3-diamineYield 44.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The compound (2.67 g) obtained in Example 22-2 was dissolved in anhydrous methanol (2.0 ml) and then added with a 4 mol/l hydrogen chloride/dioxane solution (20.0 ml), followed by stirring at room temperature for 1.5 hours. After completion of the reaction, the solvent was distilled off. Then, the residue was added with a 1 mol/l sodium hydroxide aqueous solution and extracted with dichloromethane. The extract was washed with distilled water and saturated saline solution, and then the organic layer was dried with anhydrous sodium sulfate. Subsequently, the solvent was distilled off, thereby obtaining the subject compound (726 mg) as a pale-yellow liquid.

Workup

  1. customAfter completion of the reaction
  2. distillationthe solvent was distilled off
  3. additionThen, the residue was added with a 1 mol/l sodium hydroxide aqueous solution
  4. extractionextracted with dichloromethane
  5. washThe extract was washed with distilled water and saturated saline solution
  6. dry with materialthe organic layer was dried with anhydrous sodium sulfate
  7. distillationSubsequently, the solvent was distilled off

Sources & evidence

ORD record
ord-170b7660b4e04f85ad463c9b965f1676
Source dataset
uspto-grants-2007_02
Patent number
US07176227B2

Reaction notes

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