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

HRID 15846Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 15846
[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-057144c25dbc4ca2a60aed2acbad62b6
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07732600B2

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