Propylamine → Propylaminomaleimide

HRID 929394Notes

Reaction equation

HRID 929394 reaction equation
[CH2:1]([NH2:4])[CH2:2][CH3:3].C([O-])(=O)C.[Na+].Br[C:11]1[C:12]([NH:14][C:15](=[O:17])[CH:16]=1)=[O:13]>CO>[CH2:1]([NH:4][C:11]1[C:12]([NH:14][C:15](=[O:17])[CH:16]=1)=[O:13])[CH2:2][CH3:3]

Participants

5

Reactant 3

HCID 7852PropylamineHCID 517045Sodium AcetateHCID 118195503-bromo-2,5-dihydro-1H-pyrrole-2,5-dione

Product 1

HCID 66927264PropylaminomaleimideYield 49%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

To propylamine (75 μL, 1.09 mmol) and sodium acetate (92 mg, 1.12 mmol) in methanol (15 mL) was added bromomaleimide (200 mg, 1.12 mmol) dropwise in methanol (15 mL). After 10 minutes, solvent was removed in vacuo and purification by flash chromatography (10% ethyl acetate in petroleum ether) afforded the desired compound as a bright yellow waxy solid (82 mg, 0.53 mmol) in 49% yield. δH (500 MHz, CDCl3) 7.36 (s, 1H, NH), 5.45 (s, 1H, NH), 4.80 (d, 1H, J=1.3, H-5), 3.14 (dt, 2H, J=6.2 and 7.2, H2-3), 1.71-1.63 (m, 2H, H2-2), 0.99 (t, 3H, J=7.4, H3-1); δc (125 MHz, CDCl3) 172.31 (C═O), 167.73 (C═O), 149.83 (C4), 85.29 (C5), 46.16 (C3), 21.91 (C2), 11.42 (C1); IR (solid, cm−1) 3190 (m), 2962 (m), 1693 (m), 1627 (s); MS (EI) m/z (relative intensity): 154 (M+, 60), 125 (98), 84 (100); Exact Mass Calcd for [C7H10N2O2]+ requires m/z 154.0737 Found 154.0734 (EI); UV (Acetonitrile) ε240=7400 and ε348=5700 cm−1M−1 d3.

Workup

  1. customsolvent was removed in vacuo and purification by flash chromatography (10% ethyl acetate in petroleum ether)

Sources & evidence

ORD record
ord-000ba14b3c464afca30b8cc50753fcfa
Source dataset
uspto-grants-2016_03
Patent number
US09295729B2

Reaction notes

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