2,2-Diethoxyethylamine → 2,2-Dimethoxy-n-[(1-methyl-1h-benzimidazol-2-yl)methyl]ethanamine

HRID 216285

Reaktionsgleichung

Reaktionsgleichung von HRID 216285
[CH3:1][N:2]1[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[N:4]=[C:3]1[CH:11]=O.[CH2:13]([O:15][CH:16]([O:19][CH2:20]C)[CH2:17][NH2:18])C.[BH3-]C#N.[Na+]>CO.C(O)(=O)C>[CH3:13][O:15][CH:16]([O:19][CH3:20])[CH2:17][NH:18][CH2:11][C:3]1[N:2]([CH3:1])[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[N:4]=1

Komponenten

6

Edukt 3

HCID 695242,2-DiethoxyethylamineHCID 7620841-methyl-1H-1,3-benzodiazole-2-carbaldehydeHCID 5003444Sodium cyanoborohydride

Produkt 1

HCID 552185252,2-Dimethoxy-n-[(1-methyl-1h-benzimidazol-2-yl)methyl]ethanamineAusbeute 77,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 176Acetic AcidLösungsmittelHCID 887MethanolLösungsmittel

Versuchsvorschrift

A solution of 1-methyl-2-formylbenzimidazole (1 g) in methanol (27 mL) and acetic acid (0.54 mL) was treated with aminoacetaldehyde diethylacetal (0.9 g, 1 equivalent) and NaCNBH3 (0.85 g, 2 equivalents) at 25° C., stirred for 1 hour. The mixture was partitioned between water and ethyl acetate. The organic layer was separated, washed sequentially with saturated NaHCO3 and brine, and concentrated. The residue was chromatographed on silica gel, eluting with 8% methanol/dichloromethane to give 1.2 g (64%) of the title compound.

Aufarbeitung

  1. customThe mixture was partitioned between water and ethyl acetate
  2. customThe organic layer was separated
  3. washwashed sequentially with saturated NaHCO3 and brine
  4. concentrationconcentrated
  5. customThe residue was chromatographed on silica gel
  6. washeluting with 8% methanol/dichloromethane

Quellen und Nachweise

ORD-Eintrag
ord-7e18d90a01dd45c1abefadd0378c5cef
Quelldatensatz
uspto-grants-2012_06
Patentnummer
US08193227B2

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