Sodium cyanoborohydride → N-Benzyl-4-(3,4-dihydro-2,6-naphthyridin-2(1H)-yl)-N-methylcyclohexanamine

HRID 1193364Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1193364
[CH2:1]([N:8]([CH3:16])[CH:9]1[CH2:14][CH2:13][C:12](=O)[CH2:11][CH2:10]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.Cl.[CH2:19]1[C:28]2[C:23](=[CH:24][N:25]=[CH:26][CH:27]=2)[CH2:22][CH2:21][NH:20]1.[BH3-]C#N.[Na+]>CO>[CH2:1]([N:8]([CH3:16])[CH:9]1[CH2:14][CH2:13][CH:12]([N:25]2[CH2:26][CH2:27][C:28]3[C:23](=[CH:22][CH:21]=[N:20][CH:19]=3)[CH2:24]2)[CH2:11][CH2:10]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

5

Edukt 3

HCID 5003444Sodium cyanoborohydrideHCID 220099204-[Benzyl(methyl)amino]cyclohexan-1-oneHCID 667992971,2,3,4-Tetrahydro-2,6-naphthyridine dihydrochloride

Produkt 1

HCID 66799315N-Benzyl-4-(3,4-dihydro-2,6-naphthyridin-2(1H)-yl)-N-methylcyclohexanamineAusbeute 38 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

4-(Benzyl(methyl)amino)cyclohexanone (680 mg, 3.133 mmol, 1.0 eq.) and 1,2,3,4-tetrahydro-2,6-naphthyridine dihydrochloride (713 mg, 3.44 mmol, 1.1 eq.) were dissolved in MeOH (20 ml) and the mixture was stirred for 5 hours at RT. Then the solution was cooled to 0° C., NaCNBH3 (393 mg, 3.26 mmol, 2.0 eq.) was added and the mixture was stirred for 16 hours at RT. The reaction solution was concentrated to dryness under reduced pressure and purified by column chromatography (Alox, 1.2% MeOH in DCM). Yield: 38% (400 mg, 1.194 mmol)

Aufarbeitung

  1. temperatureThen the solution was cooled to 0° C.
  2. stirringthe mixture was stirred for 16 hours at RT
  3. concentrationThe reaction solution was concentrated to dryness under reduced pressure
  4. custompurified by column chromatography (Alox, 1.2% MeOH in DCM)

Quellen und Nachweise

ORD-Eintrag
ord-fc5bfd6b36bd48b9968d2c27ed928998
Quelldatensatz
uspto-grants-2014_03
Patentnummer
US08680159B2

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