Ammonium Hydroxide → HCID 59422081, compound

HRID 1873487Notes

Reaction equation

HRID 1873487 reaction equation
[NH2:1][CH2:2][CH2:3][NH:4][C:5](=[O:26])[CH:6]([CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][O:19]C1CCCCO1)[C:7]([NH:9][CH2:10][CH2:11][NH2:12])=[O:8].O.C1(C)C=CC(S(O)(=O)=O)=CC=1.[OH-].[NH4+]>C(O)C>[NH2:1][CH2:2][CH2:3][NH:4][C:5](=[O:26])[CH:6]([CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][OH:19])[C:7]([NH:9][CH2:10][CH2:11][NH2:12])=[O:8]

Participants

5

Reactant 3

HCID 14923Ammonium HydroxideHCID 521998p-Toluenesulfonic acid monohydrateHCID 59422079HCID 59422079, compound

Product 1

HCID 59422081HCID 59422081, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
72.5 °C

Procedure

N,N′-Bis(2-aminoethyl)-2-[6-(tetrahydro-pyran-2-yloxy)-hexyl]-malonamide (3.9 g, 10.6 mmol), p-toluenesulphonic acid monohydrate (8.5 g, 3 mmol) and ethanol (50 ml) were heated under reflux at 70-75° C. for 16 hours. After cooling, concentrated ammonium hydroxide (0.880) was added dropwise until a permanent pH of 9 was achieved. The precipitated white solid was removed by filtration through Celite and the filter cake washed with ethanol (30 ml). The ethanol was removed under reduced pressure (15 mm Hg, 40° C.) to leave a semi-solid wax. This residue was subjected to chromatography on silica-gel eluting with CH2Cl2/MeOH/NH4OH (100:50:10) and the title compound found to have an rf=0.2. This product was collected and co-evaporated with ethanol (100 ml×3) to remove any residual water. A pale green viscous residue was obtained which solidifies on standing. (Yield 2.1 g, 69%).

Workup

  1. temperatureAfter cooling
  2. customThe precipitated white solid was removed by filtration through Celite
  3. washthe filter cake washed with ethanol (30 ml)
  4. customThe ethanol was removed under reduced pressure (15 mm Hg, 40° C.)
  5. customto leave a semi-solid wax
  6. washeluting with CH2Cl2/MeOH/NH4OH (100:50:10)
  7. customThis product was collected
  8. customto remove any residual water
  9. customA pale green viscous residue was obtained which

Sources & evidence

ORD record
ord-a9ee4520313243538f4ffc3a513228a4
Source dataset
uspto-grants-2012_11
Patent number
US08304388B2

Reaction notes

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