1,3-Propanediamine → HCID 18372212, compound

HRID 2301275Notes

Reaction equation

HRID 2301275 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][NH2:5].[Cl:6][C:7]1[CH:8]=[C:9]([S:14](Cl)(=[O:16])=[O:15])[CH:10]=[C:11]([Cl:13])[CH:12]=1>O1CCOCC1>[NH2:1][CH2:2][CH2:3][CH2:4][NH:5][S:14]([C:9]1[CH:8]=[C:7]([Cl:6])[CH:12]=[C:11]([Cl:13])[CH:10]=1)(=[O:16])=[O:15]

Participants

4

Reactant 2

HCID 4281,3-PropanediamineHCID 5223883,5-Dichlorobenzenesulfonyl chloride

Product 1

HCID 18372212HCID 18372212, compoundYield 29.2%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

1,3-Diaminopropane (6 g, 81.5 mmol) was dissolved in 45 ml of 1,4-dioxane, and at 15-20° C. a solution of 3,5-dichlorobenzenesulfonyl chloride (2 g, 8.15 mmol) in 5 ml of 1,4-dioxane was slowly added over 3 hours under stirring. Stirring was continued at RT. After 30 hours the formed precipitate was filtered off and the filtrate concentrated in vacuo. The residue was distributed between ethyl acetate and water. The organic layer was separated, dried with magnesium sulfate, filtered, and concentrated in vacuo to yield 2.0 g of crude material. 750 mg of this material was purified by HPLC to yield 675 mg of the title compound as TFA salt (MS=283.0 (M+H)+). 200 mg of this product was dissolved in ethyl acetate and treated with 5 ml of diluted potassium carbonate solution. The organic layer was separated, dried, filtered, and concentrated in vacuo to yield the TFA free title amine.

Workup

  1. stirringStirring
  2. customwas continued at RT
  3. filtrationAfter 30 hours the formed precipitate was filtered off
  4. concentrationthe filtrate concentrated in vacuo
  5. customThe organic layer was separated
  6. dry with materialdried with magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customto yield 2.0 g of crude material
  10. custom750 mg of this material was purified by HPLC

Sources & evidence

ORD record
ord-6da877acf9344d3a9e2ec19406ce3da7
Source dataset
uspto-grants-2002_12
Patent number
US06500803B1

Reaction notes

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