N,N-Dimethyl-1,3-propanediamine → HCID 178431611, compound

HRID 649125Notes

Reaction equation

HRID 649125 reaction equation
[CH:1]([C:3]1[C:16]([OH:17])=[C:15]([CH3:18])[C:14]([OH:19])=[C:13]2[C:4]=1[N:5]=[C:6]1[C:11](=[N:12]2)[C:10]([C:20]([O:22]C)=O)=[CH:9][CH:8]=[C:7]1[OH:24])=O.[CH3:25][N:26]([CH3:31])[CH2:27][CH2:28][CH2:29][NH2:30]>>[CH3:25][N:26]([CH3:31])[CH2:27][CH2:28][CH2:29][NH:30][C:20]([C:10]1[C:11]2[C:6](=[N:5][C:4]3[C:13]([N:12]=2)=[C:14]([OH:19])[C:15]([CH3:18])=[C:16]([OH:17])[C:3]=3[CH:1]=[N:30][CH2:29][CH2:28][CH2:27][N:26]([CH3:31])[CH3:25])[C:7]([OH:24])=[CH:8][CH:9]=1)=[O:22]

Participants

3

Reactant 2

HCID 7993N,N-Dimethyl-1,3-propanediamineHCID 178498220HCID 178498220, compound

Product 1

HCID 178431611HCID 178431611, compound

Procedure

6-Formyl-4,7,9-trihydroxy-8-methyl-1-phenazinecarboxylic acid, methyl ester (1.107 g, 3.27 mmol), was stirred with 50 g of 3-(dimethylamino)propyl amine (Aldrich Chemical Company, Milwaukee, Wis., USA) at 60° C. for 1.5 hours. The reaction mixture was then cooled in an ice bath for 20 minutes and the crude imine amide product precipitated from solution. The precipitated solid was collected by filtration and washed with 50 ml of acetonitrile. The retention time for this product, employing the HPLC system and method described in Example 3 above, was 4.6 minutes.

Workup

  1. temperatureThe reaction mixture was then cooled in an ice bath for 20 minutes
  2. customthe crude imine amide product precipitated from solution
  3. filtrationThe precipitated solid was collected by filtration
  4. washwashed with 50 ml of acetonitrile

Sources & evidence

ORD record
ord-5e9ff2e409a8472db1a73a1884059d84
Source dataset
uspto-grants-1988_04
Patent number
US04738929

Reaction notes

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