Hydrochloric Acid → alpha-N-(4-Aminophenyl)amino-epsilon-caprolactam Dihydrochloride

HRID 986877Notes

Reaction equation

HRID 986877 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([NH:10][CH:11]2[CH2:18][CH2:17][CH2:16][CH2:15][NH:14][C:12]2=[O:13])=[CH:6][CH:5]=1)([O-])=O.C1CCCCC=1.[ClH:25]>C(O)C.[Pd]>[ClH:25].[ClH:25].[NH2:1][C:4]1[CH:5]=[CH:6][C:7]([NH:10][CH:11]2[CH2:18][CH2:17][CH2:16][CH2:15][NH:14][C:12]2=[O:13])=[CH:8][CH:9]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 8079CyclohexeneHCID 70002500alpha-N-(4-Nitrophenyl)amino-epsilon-caprolactam

Product 1

HCID 22987385alpha-N-(4-Aminophenyl)amino-epsilon-caprolactam DihydrochlorideYield 81%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

2 g (8 mmol) of α-N-(4-nitrophenyl)amino-ε-caprolactam are partially dissolved in 40 ml of 95° ethanol in a 150 ml three-necked flask equipped with a thermometer and a reflux condenser. 2 g of palladium-on-charcoal (10% active and 50% moisture) are then introduced, followed by 20 ml of cyclohexene. The mixture is brought to reflux for 3 hours and is then cooled, before being filtered through celite. After having run approximately 6 ml (˜3.5 eq) of 5N hydrochloric acid onto the filtrate, the latter is evaporated to dryness and the residue is taken up in ethanol and precipitated from acetone. After filtration, 1.9 g of a white product are obtained, i.e. a final yield of 81%.

Workup

  1. customequipped with a thermometer and a reflux condenser
  2. temperatureto reflux for 3 hours
  3. temperatureis then cooled
  4. filtrationbefore being filtered through celite
  5. customthe latter is evaporated to dryness
  6. customprecipitated from acetone
  7. filtrationAfter filtration, 1.9 g of a white product
  8. customare obtained

Sources & evidence

ORD record
ord-f00b0c3f0c744a8dbb02e34a15919769
Source dataset
uspto-grants-2003_10
Patent number
US06630004B1

Reaction notes

Loading…