Propylamine → N-Methyl propylaminomaleimide

HRID 929396Notes

Reaction equation

HRID 929396 reaction equation
[CH2:1]([NH2:4])[CH2:2][CH3:3].C([O-])(=O)C.[Na+].[CH3:10][N:11]1[C:15](=[O:16])[CH:14]=[C:13](Br)[C:12]1=[O:18]>CO>[CH3:10][N:11]1[C:15](=[O:16])[CH:14]=[C:13]([NH:4][CH2:1][CH2:2][CH3:3])[C:12]1=[O:18]

Participants

5

Reactant 3

HCID 7852PropylamineHCID 517045Sodium AcetateHCID 12136311N-methyl bromomaleimide

Product 1

HCID 68150162N-Methyl propylaminomaleimideYield 31%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

To propylamine (52 μL, 0.78 mmol) and sodium acetate (64 mg, 0.78 mmol) in methanol (30 mL) was added N-methylmonobromomaleimide (150 mg, 0.78 mmol) dropwise in methanol (30 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 (41 mg, 0.24 mmol) in 31% yield. δH (500 MHz, CDCl3) 5.43 (s, 1H, NH), 4.80 (s, 1H, H-2), 3.16-3.13 (m, 2H, H2-9), 2.98 (s, 3H, H3-6), 1.71-1.64 (m, 2H, H2-8), 0.99 (t, J=7.5, H3-7); δC (125 MHz, CDCl3) 172.71 (C═O), 167.66 (C═O), 149.51 (C3), 83.84 (C2), 46.01 (C9), 23.44 (C6), 21.87 (C8), 11.38 (C7); IR (film, cm−1) 3317 (m), 2944 (w), 1698 (s), 1651 (s); MS (EI) m/z (relative intensity): 168 (M+, 70), 139 (100), 111 (40); Exact Mass Calcd for [C8H12N2O2]+ requires m/z 168.0893 Found 168.0887 (EI); UV (Acetonitrile) ε210=15900, ε240=2800, ε283=500 and ε368=500 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-b3b57da2d9104814b945134875a1f65a
Source dataset
uspto-grants-2016_03
Patent number
US09295729B2

Reaction notes

Loading…