Octylamine → 1-Nonyl-3-(octylamino)pyrrolidine-2,5-dione

HRID 1016519Notes

Reaction equation

HRID 1016519 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].[CH2:17]([NH2:25])[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24].C(N(CC)CC)C>C(#N)C>[CH2:1]([N:10]1[C:11](=[O:16])[CH2:12][CH:13]([NH:25][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])[C:14]1=[O:15])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH3:9]

Participants

5

Reactant 3

HCID 8143OctylamineHCID 8471TriethylamineHCID 512831N-Nonylmaleimide

Product 1

HCID 5128381-Nonyl-3-(octylamino)pyrrolidine-2,5-dione

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of N-nonyl maleimide (0.01 M) prepared as described in Example 12 above, octylamine (0.01 M), triethylamine [catalytic, 0.1 equivalent] in acetonitrile (25 ml) was stirred for 24 hours at room temperature. Acetonitrile was removed under vacuum to leave a residual liquid product which was flash chromatographed (25% ethyl acetate in petroleum ether) to yield a white solid as the desired product.

Workup

  1. customprepared
  2. customAcetonitrile was removed under vacuum
  3. customto leave a residual liquid product which
  4. customchromatographed (25% ethyl acetate in petroleum ether)

Sources & evidence

ORD record
ord-e3d5b4af17484a988757e55c13e80643
Source dataset
uspto-grants-2002_11
Patent number
US06476053B1

Reaction notes

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