1,3-Propanediamine → N-(2-aminophenyl)-6-(3-aminopropylamino)nicotinamide

HRID 1695032Notes

Reaction equation

HRID 1695032 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][C:9](=[O:17])[C:10]1[CH:15]=[CH:14][C:13](Cl)=[N:12][CH:11]=1.[CH2:18]([NH2:22])[CH2:19][CH2:20][NH2:21]>>[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][C:9](=[O:17])[C:10]1[CH:15]=[CH:14][C:13]([NH:21][CH2:20][CH2:19][CH2:18][NH2:22])=[N:12][CH:11]=1

Participants

3

Reactant 2

HCID 4281,3-PropanediamineHCID 22478760N-(2-aminophenyl)-6-chloronicotinamide

Product 1

HCID 57993723N-(2-aminophenyl)-6-(3-aminopropylamino)nicotinamideYield 59%

Procedure

N-(2-Aminophenyl)-6-chloronicotinamide (248 mg, 1 mmol) and 6 ml of 1,3-propanediamine were heated to 80° C. for 3 hours. The excess 1,3-propanediamine was removed under vacuum. To the residue was added 5 ml of 0.20 M NaOH. The mixture was extracted with 100 ml of ethyl acetate. The ethyl acetate was removed under vacuum to give the title compound (168 mg, 59% yield) as a brown solid. LC-MS (m/z) 286 (M+1).

Workup

  1. customThe excess 1,3-propanediamine was removed under vacuum
  2. additionTo the residue was added 5 ml of 0.20 M NaOH
  3. extractionThe mixture was extracted with 100 ml of ethyl acetate
  4. customThe ethyl acetate was removed under vacuum

Sources & evidence

ORD record
ord-8fd714b20f5c45d88a5afc5b2d650c88
Source dataset
uspto-grants-2012_04
Patent number
US08158656B2

Reaction notes

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