Dimethylamine → N-(5,6-Dihydro-6-oxo-2-phenanthridinyl)-2-(dimethylamino)acetamide

HRID 2086010Notes

Reaction equation

HRID 2086010 reaction equation
Cl[CH2:2][C:3]([NH:5][C:6]1[CH:19]=[CH:18][C:17]2[NH:16][C:15](=[O:20])[C:14]3[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=3)[C:8]=2[CH:7]=1)=[O:4].[CH3:21][NH:22][CH3:23].P([O-])([O-])([O-])=O.[K+].[K+].[K+]>CN(C)C=O>[O:20]=[C:15]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[C:8]2[CH:7]=[C:6]([NH:5][C:3](=[O:4])[CH2:2][N:22]([CH3:23])[CH3:21])[CH:19]=[CH:18][C:17]=2[NH:16]1

Participants

5

Reactant 3

HCID 674Dimethylamine2×HCID 62657Potassium Phosphate, TribasicHCID 9814438N-(6-oxo-5,6-dihydro-phenanthridin-2-yl)-chloroacetamide2×

Product 1

HCID 4858N-(5,6-Dihydro-6-oxo-2-phenanthridinyl)-2-(dimethylamino)acetamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Prepared from the compound of Example 2 and dimethylamine. To a solution of 2-chloro-N-(5,6-dihydro-6-oxo-2-phenanthridinyl)-acetamide (635 mg) in N,N-dimethylformamide (100 mL) was added potassium phosphate (918 mg) and dimethylamine (1.3 ml, 2 molar soln.). The solution stirred at room temperature for 5 hours followed by evaporation of the solvent. The light brown product was washed with water and filtered. Concentrated HCl (0.3 mL) was added to a solution of the product in dioxane (150 mL) to precipitate the hydrogen chloride salt (400 mg), mp>300° C. 1H-NMR (300 MHz, DMSO-d6), 11.63 (br s, 1H), 10.92 (br s, 1H), 8.63 (s, 1H), 8.35 (d, J=9.0 Hz, 1H), 8.26 (d, J=9.0 Hz, 1H), 7.91 (t, J=9.0 Hz, 1H), 7.69 (m, 2H), 7.38 (d, J=9.0 Hz, 1H), 4.19 (br s, 2H), 2.91 (br s, 6H). Anal. (C17H17N3O2.HCl 0.9 H2O), Calc for: C, 58.67; H, 5.73; N, 12.07; Cl, 10.19. Found: C, 58.91; H, 5.59; N, 11.80; Cl, 9.95.

Workup

  1. customfollowed by evaporation of the solvent
  2. washThe light brown product was washed with water
  3. filtrationfiltered
  4. additionConcentrated HCl (0.3 mL) was added to a solution of the product in dioxane (150 mL)
  5. customto precipitate the hydrogen chloride salt (400 mg), mp>300° C

Sources & evidence

ORD record
ord-27cefa0987a546298838393cab806065
Source dataset
uspto-grants-2004_04
Patent number
US06723733B2

Reaction notes

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