Sodium triacetoxyborohydride → 2-Methyl-5-{4-[2-(3-nitrophenyl)propyl]-1-piperazinyl}quinoline

HRID 734566Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 734566
[N+:1]([C:4]1[CH:5]=[C:6]([CH:10]([CH3:13])[CH:11]=O)[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2].[CH3:14][C:15]1[CH:24]=[CH:23][C:22]2[C:17](=[CH:18][CH:19]=[CH:20][C:21]=2[N:25]2[CH2:30][CH2:29][N:28](CCC3C=C(C=CC=3)N)[CH2:27][CH2:26]2)[N:16]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C(Cl)Cl>[CH3:14][C:15]1[CH:24]=[CH:23][C:22]2[C:17](=[CH:18][CH:19]=[CH:20][C:21]=2[N:25]2[CH2:30][CH2:29][N:28]([CH2:11][CH:10]([C:6]3[CH:7]=[CH:8][CH:9]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=3)[CH3:13])[CH2:27][CH2:26]2)[N:16]=1

Komponenten

5

Edukt 3

HCID 5049666Sodium triacetoxyborohydrideHCID 226741372-(3-Nitrophenyl)propanalHCID 498521053-(2-[4-(2-Methyl-5-quinolinyl)-1-piperazinyl]ethyl}aniline

Produkt 1

HCID 574443342-Methyl-5-{4-[2-(3-nitrophenyl)propyl]-1-piperazinyl}quinolineAusbeute 133,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A mixture of 2-(3-nitrophenyl)propanal (1.2 equiv. 50 mg), 2-methyl-5-(1-piperazinyl)quinoline (D3) (52 mg) and DCM (2 mL) was stirred for 1 h. Sodium triacetoxyborohydride (1.2 equiv., 58 mg) was added and the resulting mixture was stirred for 18 h. The reaction mixture was concentrated in vacuo and purified using ion-exchange chromatography (SCX-2), eluting with methanol followed by ammonia in methanol (1M). The basic fractions were concentrated under vacuum and purified by chromatography (SPE, SiO2) using DCM-methanol (98:2) as eluent to afford the title compound as yellow liquid (78 mg, 78% yield).

Aufarbeitung

  1. stirringthe resulting mixture was stirred for 18 h
  2. concentrationThe reaction mixture was concentrated in vacuo
  3. custompurified
  4. washeluting with methanol
  5. concentrationThe basic fractions were concentrated under vacuum
  6. custompurified by chromatography (SPE, SiO2)

Quellen und Nachweise

ORD-Eintrag
ord-6e5956d0f72c47769561f21251436165
Quelldatensatz
uspto-grants-2009_09
Patentnummer
US07592346B2

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