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N,N-bis(3-aminopropyl)methylamine → N1-Methyl-N3-(3-methyl-4-nitrophenyl)-N1-{3-[(3-methyl-4-nitrophenyl)amino]propyl}-1,3-propanediamine

HRID 68177
Notes
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Reaction equation

HRID 68177 reaction equation
F[C:2]1[CH:3]=[CH:4][C:5]([N+:9]([O-:11])=[O:10])=[C:6]([CH3:8])[CH:7]=1.C(=O)([O-])[O-].[Na+].[Na+].[CH3:18][N:19]([CH2:24][CH2:25][CH2:26][NH2:27])[CH2:20][CH2:21][CH2:22][NH2:23]>C1(C)C=CC=CC=1>[CH3:18][N:19]([CH2:24][CH2:25][CH2:26][NH:27][C:2]1[CH:3]=[CH:4][C:5]([N+:9]([O-:11])=[O:10])=[C:6]([CH3:8])[CH:7]=1)[CH2:20][CH2:21][CH2:22][NH:23][C:2]1[CH:3]=[CH:4][C:5]([N+:9]([O-:11])=[O:10])=[C:6]([CH3:8])[CH:7]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 7777N,N-bis(3-aminopropyl)methylamineHCID 10340Sodium CarbonateHCID 949565-Fluoro-2-nitrotoluene

Product 1

HCID 86731947N1-Methyl-N3-(3-methyl-4-nitrophenyl)-N1-{3-[(3-methyl-4-nitrophenyl)amino]propyl}-1,3-propanediamine

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

To 5-fluoro-2-nitrotoluene (50.0 g, 0.32 mol) was added sodium carbonate (17.1 g, 0.16 mol) at 60° C. 3,3′-Diamino-N-methyldipropylamine (23.7 g, 0.16 mol) was then carefully added dropwise (exothermic reaction). The resulting mixture was heated at 100° C. for 12 hours. 100 ml toluene were added to the cooled reaction mixture causing the inorganic salts to precipitate, which were filtered off. The organic phase was then concentrated down under vacuum in a rotovap to afford the product as a residue in the form of a yellow orange oil. Yield: 52.5 g (78.4%); 1H-NMR (400 MHz, DMSO-d6): δ [ppm]=1.71 (m, 4H); 2.18 (s, 3H); 2.40 (m, 4H); 2.55 (s, 6H); 3.17 (m, 4H); 6.45 (s, 2H); 6.48 (d, 2H); 7.08 (br., 2×NH); 7.92 (d, 2H).

Workup

  1. custom(exothermic reaction)
  2. customto precipitate
  3. filtrationwhich were filtered off
  4. concentrationThe organic phase was then concentrated down under vacuum in a rotovap
  5. customto afford the product as a residue in the form of a yellow orange oil

Sources & evidence

ORD record
ord-727ba28406384fee9d438a866f21cfd8
Source dataset
uspto-grants-2014_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08821592B1

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes