Acetic Acid → N2,N2-Diethyl-1-[4-(propylsulphonyl)phenyl]ethane-1,2-diamine

HRID 1698510Notes

Reaction equation

HRID 1698510 reaction equation
C([N:4](CC=C)[CH:5]([C:8]1[CH:13]=[CH:12][C:11]([S:14]([CH2:17][CH2:18][CH3:19])(=[O:16])=[O:15])=[CH:10][CH:9]=1)[CH2:6][NH2:7])C=C.[CH:23](=O)[CH3:24].[C:26](O)(=O)[CH3:27].C([BH3-])#N.[Na+].CN1C(=O)CC(=O)N(C)C1=O>CO>[CH2:26]([N:7]([CH2:23][CH3:24])[CH2:6][CH:5]([C:8]1[CH:9]=[CH:10][C:11]([S:14]([CH2:17][CH2:18][CH3:19])(=[O:15])=[O:16])=[CH:12][CH:13]=1)[NH2:4])[CH3:27]

Participants

7

Reactant 5

HCID 176Acetic AcidHCID 177AcetaldehydeHCID 69860Dimethylbarbituric acidHCID 5003444Sodium cyanoborohydrideHCID 86635958N1,N1-Diallyl-1-[4-(propylsulphonyl)phenyl]ethane-1,2-diamine

Product 1

HCID 86635961N2,N2-Diethyl-1-[4-(propylsulphonyl)phenyl]ethane-1,2-diamineYield 75%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of N1,N1-diallyl-1-[4-(propylsulphonyl)phenyl]ethane-1,2-diamine (473 mg, 1.47 mmol, prepared as described in Example 47c in methanol (10 mL) was added acetaldehyde (approximately 0.5 mL, approx. 9 mmol), acetic acid (0.42 mL, 7.3 mmol) and finally, sodium cyanoborohydride (203 mg, 3.2 mmol). The mixture was stirred at room temperature, under nitrogen, overnight and then quenched by addition of satd. NaHCO3(aq). Methanol was removed in vacuo, the residue diluted with water and the product extracted into ethyl acetate (×3). The combined organic extracts were washed with brine, dried (MgSO4) and concentrated. The crude material was dissolved in dichloromethane and to this solution was added 1,3-dimethylbarbituric acid (1.37 g, 8.8 mmol) and palladium (tetrakis)triphenylphosphine (85 mg, 0.07 mmol). The mixture was heated at reflux for 6 h, then cooled and concentrated. The title compound was partially purified using an SCX cartridge (330 mg obtained, 75% yield over two steps, approximate since not pure). m/z (ES+) 282 (M−NH2).

Workup

  1. customquenched by addition of satd
  2. customMethanol was removed in vacuo
  3. additionthe residue diluted with water
  4. extractionthe product extracted into ethyl acetate (×3)
  5. washThe combined organic extracts were washed with brine
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated
  8. dissolutionThe crude material was dissolved in dichloromethane and to this solution
  9. temperatureThe mixture was heated
  10. temperatureat reflux for 6 h
  11. temperaturecooled
  12. concentrationconcentrated
  13. customThe title compound was partially purified
  14. customobtained

Sources & evidence

ORD record
ord-06db2de093b643c2bddef3976a901211
Source dataset
uspto-grants-2012_04
Patent number
US08163956B2

Reaction notes

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