Hexamethylenediamine → N-(2-aminophenyl)-6-(6-aminohexylamino)nicotinamide

HRID 1695073Notes

Reaction equation

HRID 1695073 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.[NH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][NH2:25]>>[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:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][NH2:25])=[N:12][CH:11]=1

Participants

3

Reactant 2

HCID 16402HexamethylenediamineHCID 22478760N-(2-aminophenyl)-6-chloronicotinamide

Product 1

HCID 57993736N-(2-aminophenyl)-6-(6-aminohexylamino)nicotinamideYield 67%

Procedure

N-(2-Aminophenyl)-6-chloronicotinamide (248 mg, 1 mmol) and 1,6-diaminohexane (5.80 g, 50 mmol) were heated to 80° C. for 3 hours. The excess 1,6-diaminohexane 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 (219 mg, 67% yield) as a brown solid. LC-MS (m/z) 328 (M+1).

Workup

  1. customThe excess 1,6-diaminohexane 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-6c7f31061296467992b45bfe8c4455c6
Source dataset
uspto-grants-2012_04
Patent number
US08158656B2

Reaction notes

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