Hydrochloric Acid → 3-[2-(Dibutylamino)ethylamino]-1-nonyl-pyrrolidine-2,5-dione

HRID 1016524Notes

Reaction equation

HRID 1016524 reaction equation
[CH2:1]([N:10]1[C:14](=[O:15])[CH:13]=[CH:12][C:11]1=[O:16])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH3:9].C(N(CC)CC)C.[CH2:24]([N:28]([CH2:32][CH2:33][CH2:34][CH3:35])[CH2:29][CH2:30][NH2:31])[CH2:25][CH2:26][CH3:27].Cl>C(#N)C.C(OCC)(=O)C>[CH2:24]([N:28]([CH2:32][CH2:33][CH2:34][CH3:35])[CH2:29][CH2:30][NH:31][CH:13]1[CH2:12][C:11](=[O:16])[N:10]([CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH3:9])[C:14]1=[O:15])[CH2:25][CH2:26][CH3:27]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 77062N,N-DibutylethylenediamineHCID 512831N-Nonylmaleimide

Product 1

HCID 5128573-[2-(Dibutylamino)ethylamino]-1-nonyl-pyrrolidine-2,5-dione

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

N-nonyl maleimide (0.02 mM) prepared as described in Example 12 above in 2 ml of acetonitrile was treated with one equivalent of triethylamine and one equivalent of N,N-dibutylethylenediamine. The reaction mixture was stirred for six hours and then the acetonitrile was evaporated. The residue obtained was treated with cold aqueous dilute hydrochloric acid solution and ethyl acetate, with stirring for one hour. The ethyl acetate layer was then separated and concentrated to give the desired product.

Workup

  1. customthe acetonitrile was evaporated
  2. customThe residue obtained
  3. stirringwith stirring for one hour
  4. customThe ethyl acetate layer was then separated
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-d2a58ec7360943a4acba299008de7e77
Source dataset
uspto-grants-2002_11
Patent number
US06476053B1

Reaction notes

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