Potassium Carbonate → N3-(3-Pyrrolidin-1-yl-propyl)-pyridine-3,4-diamine

HRID 494745Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 494745
Br[C:2]1[CH:3]=[N+:4]([O-])[CH:5]=[CH:6][C:7]=1[N+:8]([O-])=O.[N:12]1([CH2:17][CH2:18][CH2:19][NH2:20])[CH2:16][CH2:15][CH2:14][CH2:13]1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C.CCO.[Pd]>[N:12]1([CH2:17][CH2:18][CH2:19][NH:20][C:2]2[CH:3]=[N:4][CH:5]=[CH:6][C:7]=2[NH2:8])[CH2:16][CH2:15][CH2:14][CH2:13]1

Komponenten

7

Edukt 3

HCID 11430Potassium CarbonateHCID 316701-PyrrolidinepropanamineHCID 5485213-Bromo-4-nitropyridine N-oxide

Produkt 1

HCID 85865444N3-(3-Pyrrolidin-1-yl-propyl)-pyridine-3,4-diamine

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 23938PalladiumKatalysatorHCID 702EthanolLösungsmittelHCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

1.300 g (5.940 mmol) 3-bromo-4-nitro-pyridine-1-oxide and 0.980 g (7.430 mmol) 3-pyrrolidin-1-yl-propylamine was added to a suspension of 0.820 g (5.940 mmol) potassium carbonate in 20 mL DMF and the mixture was stirred for 3 hours at 90° C. The solvent was evaporated i. vac. and the residue purified by column chromatography (Alox (neutral, activity II-III), gradient dichloromethane/MeOH 100:0→95:5 v/v) (0.950 g, 60% of theory). 0.900 g (3.380 mmol) of the intermediate product was added to a suspension of 300 mg Pd/C in 10 mL EtOH and the mixture was hydrogenated for 4.5 hours at RT and 50 psi H2-pressure. The catalyst was removed by filtration and the filtrate evaporated i. vac. The product is present in admixture with the corresponding pyridine-N-oxide and was used in the next reaction step without any further purification.

Aufarbeitung

  1. customThe solvent was evaporated i
  2. customand the residue purified by column chromatography (Alox (neutral, activity II-III), gradient dichloromethane/MeOH 100:0→95:5 v/v) (0.950 g, 60% of theory)
  3. waitthe mixture was hydrogenated for 4.5 hours at RT
  4. customThe catalyst was removed by filtration
  5. customthe filtrate evaporated i
  6. customwas used in the next reaction step without any further purification

Quellen und Nachweise

ORD-Eintrag
ord-d46c52631fc44624b590825efb5a55d7
Quelldatensatz
uspto-grants-2009_05
Patentnummer
US07538115B2

Notizen zur Reaktion

Wird geladen…