1-Chloro-4-(chloromethyl)benzene → 2-[N-(3-aminopropyl)-N-(4-chlorobenzyl)amino]pyridine

HRID 464349Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 464349
[H-].[Na+].[NH2:3][CH2:4][CH2:5][CH2:6][NH:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][N:9]=1.[H][H].[Cl:16][C:17]1[CH:24]=[CH:23][C:20]([CH2:21]Cl)=[CH:19][CH:18]=1>CS(C)=O.O>[NH2:3][CH2:4][CH2:5][CH2:6][N:7]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][N:9]=1)[CH2:21][C:20]1[CH:23]=[CH:24][C:17]([Cl:16])=[CH:18][CH:19]=1

Komponenten

7

Edukt 4

HCID 77231-Chloro-4-(chloromethyl)benzeneHCID 24758Sodium hydrideHCID 10606924N-(3-aminopropyl)pyridin-2-amineHCID 178418361HCID 178418361, Verbindung

Produkt 1

HCID 198610762-[N-(3-aminopropyl)-N-(4-chlorobenzyl)amino]pyridine

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 679Dimethyl SulfoxideLösungsmittel2×HCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
85 °C

Versuchsvorschrift

A mixture of sodium hydride (1.12 g) and 2-(3-amino-propylamino) pyridine (7.05 g) in DMSO (30 ml) was heated slowly to 85° C. under nitrogen. After the evolution of hydrogen had ceased the solution was cooled to room temperature and 4-chlorobenzyl chloride (5.95 ml) in DMSO (10 ml) added dropwise keeping the temperature below 30° C. After standing for 72 hr, water (300 ml) was added and the mixture extracted with ether. The extract was washed with water and 2N hydrochloric acid. The pH of the acid washing was raised to 6 and extracted with ether. The pH was raised further to 14 and extracted again with ether. After drying (MgSO4) and stripping, the final ether extract gave 2-[N-(3-aminopropyl)-N-(4-chlorobenzyl)amino]pyridine (7.43 g) as an oil, bp 160° C. 0.04 mm Hg. (ii) 2-[N-(3-aminopropyl)-N-(4-chlorobenzyl)amino]pyridine (1.25 g) and 2-nitroamino-5-(6-methylpyrid-3-ylmethyl)pyrimid-4-one (1.08 g) were heated together under reflux in pyridine (10ml) for 20 hr. On cooling, the mixture was stripped, the residue triturated with wet ether and recrystallised from isopropanol/water to give 2-[3-[N-(4-chlorobenzyl)-N-pyrid-2-ylamino]propylamino]-5-(6-methyl-pyrid-3-ylmethyl) pyrimid-4-one 1H2O, 1.68 g (83%) mp 88°-92° C.

Aufarbeitung

  1. temperaturewas cooled to room temperature
  2. customthe temperature below 30° C
  3. extractionthe mixture extracted with ether
  4. washThe extract was washed with water and 2N hydrochloric acid
  5. washThe pH of the acid washing
  6. temperaturewas raised to 6
  7. extractionextracted with ether
  8. temperatureThe pH was raised further to 14
  9. extractionextracted again with ether
  10. dry with materialAfter drying (MgSO4)
  11. extractionthe final ether extract

Quellen und Nachweise

ORD-Eintrag
ord-9a82250afa42481b88c3282643cbbefb
Quelldatensatz
uspto-grants-1985_10
Patentnummer
US04547506

Notizen zur Reaktion

Wird geladen…