Potassium Carbonate → HCID 66599575, compound

HRID 1909023Notes

Reaction equation

HRID 1909023 reaction equation
Cl[C:2]1[CH:3]=[CH:4][C:5]([N+:9]([O-:11])=[O:10])=[C:6]([CH:8]=1)[NH2:7].[CH3:12][N:13]([CH3:20])[CH:14]1[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[NH2:7][C:6]1[CH:8]=[C:2]([N:17]2[CH2:18][CH2:19][CH:14]([N:13]([CH3:20])[CH3:12])[CH2:15][CH2:16]2)[CH:3]=[CH:4][C:5]=1[N+:9]([O-:11])=[O:10]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 742185-Chloro-2-nitroanilineHCID 417391N,N-Dimethylpiperidin-4-amine

Product 1

HCID 66599575HCID 66599575, compoundYield 87.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
140 °C

Procedure

To 5-chloro-2-nitroaniline (16.9 mmol) in DMF (56 mL) was added 4-(dimethylamino)piperidine (18.5 mmol) and K2CO3 (18.5 mmol). The reaction was stirred at 140° C. overnight after which another further 9.2 mmol of the amine was added. Stirring at 140° C. was continued for a further 5 hours. The mixture was allowed to cool and then the precipitate was collected by filtration. The precipitate was washed with EtOAc and then the combined filtrates were evaporated to dryness. The residue suspended in water and the resulting precipitate collected by filtration. The product was washed with water and then dried to give a [1-(3-amino-4-nitro-phenyl)-piperidin-4-yl]-dimethyl-amine as a brown/orange solid (3.9 g).

Workup

  1. additionwas added
  2. temperatureto cool
  3. filtrationthe precipitate was collected by filtration
  4. washThe precipitate was washed with EtOAc
  5. customthe combined filtrates were evaporated to dryness
  6. filtrationthe resulting precipitate collected by filtration
  7. washThe product was washed with water
  8. customdried

Sources & evidence

ORD record
ord-c3dd0051d5a64859a48e466fa4aa7d97
Source dataset
uspto-grants-2013_12
Patent number
US08598217B2

Reaction notes

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