Putrescine → HCID 89824741, compound

HRID 526671Notes

Reaction equation

HRID 526671 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][CH2:5][NH2:6].C([O-])([O-])=O.[K+].[K+].[C:13]([O:17][C:18]([N:20]([CH3:30])[CH2:21][CH2:22][CH2:23][CH2:24]OS(C)(=O)=O)=[O:19])([CH3:16])([CH3:15])[CH3:14]>C(#N)C>[C:13]([O:17][C:18](=[O:19])[N:20]([CH2:21][CH2:22][CH2:23][CH2:24][NH:1][CH2:2][CH2:3][CH2:4][CH2:5][NH2:6])[CH3:30])([CH3:16])([CH3:15])[CH3:14]

Participants

5

Reactant 3

HCID 1045PutrescineHCID 11430Potassium CarbonateHCID 50994451HCID 50994451, compound

Product 1

HCID 89824741HCID 89824741, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

Putrescine (9.45 g, 107 mmol) was dissolved in acetonitrile (200 mL) with K2CO3 (14.79 g, 107 mmol) and stirred under N2. Mesylate 22 (6.03 g, 21.4 mmol) dissolved in acetonitrile (60 mL) was added dropwise over 30 min while stirring under N2. After 30 min, the reaction mixture was brought to reflux and stirred overnight. The reaction mixture was then cooled, solid K2CO3 was filtered off and the filtrate concentrated in vacuo. The residue was re-dissolved in CH2Cl2 (200 mL) and washed six times with sat. aqueous Na2CO3 to remove the unreacted putrescine. The organic layer was then dried over anhydrous Na2SO4, filtered, and concentrated to give the product 23 as a clear oil that was used in the next step without further purification, yield: 5.31 g (90%); 1H NMR (CDCl3) δ 3.21 (t, 2H), 2.84 (s, 3H), 2.71 (t, 2H), 2.62 (t, 4H), 1.40-1.60 (m, 17H).

Workup

  1. additionwas added dropwise over 30 min
  2. stirringwhile stirring under N2
  3. temperatureto reflux
  4. stirringstirred overnight
  5. temperatureThe reaction mixture was then cooled
  6. filtrationsolid K2CO3 was filtered off
  7. concentrationthe filtrate concentrated in vacuo
  8. dissolutionThe residue was re-dissolved in CH2Cl2 (200 mL)
  9. washwashed six times with sat. aqueous Na2CO3
  10. customto remove the unreacted putrescine
  11. dry with materialThe organic layer was then dried over anhydrous Na2SO4
  12. filtrationfiltered
  13. concentrationconcentrated

Sources & evidence

ORD record
ord-d2b544a0ce9c4bccb046d45aad73bdac
Source dataset
uspto-grants-2016_05
Patent number
US09346741B2

Reaction notes

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