1-(3-Chlorophenyl)piperazine → 5-[4-(3-Chloro-phenyl)-piperazin-1-ylmethyl]-pyrimidine-2,4-diamine

HRID 2294040

Reaktionsgleichung

Reaktionsgleichung von HRID 2294040
[Cl:1][C:2]1[CH:3]=[C:4]([N:8]2[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]2)[CH:5]=[CH:6][CH:7]=1.C(N(CC)CC)C.Br.Br.Br[CH2:24][C:25]1[C:26]([NH2:32])=[N:27][C:28]([NH2:31])=[N:29][CH:30]=1>O1CCCC1>[Cl:1][C:2]1[CH:3]=[C:4]([N:8]2[CH2:13][CH2:12][N:11]([CH2:24][C:25]3[C:26]([NH2:32])=[N:27][C:28]([NH2:31])=[N:29][CH:30]=3)[CH2:10][CH2:9]2)[CH:5]=[CH:6][CH:7]=1

Komponenten

5

Edukt 3

HCID 13551-(3-Chlorophenyl)piperazineHCID 8471TriethylamineHCID 214736085-(Bromomethyl)pyrimidine-2,4-diamine dihydrobromide

Produkt 1

HCID 214736735-[4-(3-Chloro-phenyl)-piperazin-1-ylmethyl]-pyrimidine-2,4-diamineAusbeute 63 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A solution of 13.5 g (0.050 mol) of 1-(3-chloro-phenyl)-piperazine in 500 ml of tetrahydrofuran was treated with 35 ml (0.25 mol) of triethylamine and 18.2 g (0.050 mol) of 5-bromomethyl-pyrimidine-2,4-diamine dihydrobromide and the mixture was stirred at room temperature under argon for 16 hours. The suspension obtained was suction filtered and the filtrate was completely freed from the solvents. The residue was chromatographed over silica gel with acetonitrile/methanol 1:1 as the eluent and digested in diethyl ether. 10 g (63%) of 5-[4-(3-chloro-phenyl)-piperazin-1-ylmethyl]-pyrimidine-2,4-diamine were obtained as beige crystals; m.p. 222°-226°.

Aufarbeitung

  1. customThe suspension obtained
  2. filtrationfiltered
  3. customThe residue was chromatographed over silica gel with acetonitrile/methanol 1:1 as the eluent and digested in diethyl ether

Quellen und Nachweise

ORD-Eintrag
ord-82a69ec5510545d78b21805f22dd62c6
Quelldatensatz
uspto-grants-1997_11
Patentnummer
US05688798

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