Benzylethanolamine → 2-[Benzyl({5-[benzyl(1-methylethyl)amino]-3-chloropyrazin-2-yl}methyl)amino]ethanol

HRID 2188674Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2188674
C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[CH2:15]([N:22]([CH:32]([CH3:34])[CH3:33])[C:23]1[N:24]=[C:25]([Cl:31])[C:26]([CH:29]=O)=[N:27][CH:28]=1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.[CH2:35]([NH:42][CH2:43][CH2:44][OH:45])[C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1.C(=O)([O-])O.[Na+]>C(#N)C.C(O)(=O)C>[CH2:35]([N:42]([CH2:29][C:26]1[C:25]([Cl:31])=[N:24][C:23]([N:22]([CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH:32]([CH3:34])[CH3:33])=[CH:28][N:27]=1)[CH2:43][CH2:44][OH:45])[C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1

Komponenten

7

Edukt 4

HCID 4348BenzylethanolamineHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 866489995-[Benzyl(1-methylethyl)amino]-3-chloropyrazine-2-carbaldehyde

Produkt 1

HCID 866490002-[Benzyl({5-[benzyl(1-methylethyl)amino]-3-chloropyrazin-2-yl}methyl)amino]ethanolAusbeute 94 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 176Acetic AcidLösungsmittelHCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

Sodium triacetoxyborohydride (2.65 g) was added to a solution of 5-[benzyl(1-methylethyl)amino]-3-chloropyrazine-2-carbaldehyde (2.42 g), N-benzylethanolamine (1.42 g) and acetic acid (1.43 mL) in acetonitrile (14 mL), and the mixture was stirred at room temperature for 16 hr. The reaction mixture was basified with saturated aqueous sodium hydrogen carbonate solution, and extracted with ethyl acetate. The aqueous layer was extracted again with ethyl acetate. The combined organic layer was washed with water and saturated brine, dried over magnesium sulfate, and concentrated. The residue was purified by silica gel column chromatography (solvent gradient: 20→50% ethyl acetate/hexane) to give the title compound (3.32 g, 94%) as a pale-yellow oil.

Aufarbeitung

  1. extractionextracted with ethyl acetate
  2. extractionThe aqueous layer was extracted again with ethyl acetate
  3. washThe combined organic layer was washed with water and saturated brine
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated
  6. customThe residue was purified by silica gel column chromatography (solvent gradient: 20→50% ethyl acetate/hexane)

Quellen und Nachweise

ORD-Eintrag
ord-a06c0b3a0999491097069c7eab16c87b
Quelldatensatz
uspto-grants-2012_12
Patentnummer
US08324201B2

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