Sodium borohydride → [(1,2-dimethyl-1H-indol-3-yl)methyl](methyl)amine

HRID 1921032Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1921032
[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]([CH:11]=[N:12][CH3:13])=[C:3]1[CH3:14].[BH4-].[Na+]>C(O)C>[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]([CH2:11][NH:12][CH3:13])=[C:3]1[CH3:14]

Komponenten

4

Edukt 2

HCID 4311764Sodium borohydrideHCID 141422191,2-Dimethyl-3-(methyliminomethyl)-1H-indole

Produkt 1

HCID 10877907[(1,2-dimethyl-1H-indol-3-yl)methyl](methyl)amineAusbeute 68 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

1,2-Dimethyl-3-(methyliminomethyl)-1H-indole was taken up in ethanol (200 mL) and NaBH4 (2.6 g, 68.7 mmole) was added portionwise with stirring at RT (vigorous gas evolution). After 16 h the reaction was concentrated under vacuum, and the residue was basified with aqueous 1.0 N NaOH (200 mL). The mixture was extracted with Et2O (250 mL), and the combined Et2O extracts were washed with brine, dried (Na2SO4) and concentrated. Purification by flash chromatography on silica gel (5-10% (5% NH4OH/MeOH)/CHCl3) gave the title compound (8.47 g, 68%) as an oil which solidified in the freezer 1H NMR (400 MHz, CDCl3) δ 7.60 (d, J=7.7 Hz, 1H), 7.29 (d, J=8.0 Hz, 1H), 7.19 (t, 1H), 7.12 (t, 1H), 3.93 (s, 2H), 3.69 (s, 3H), 2.49 (s, 3H), 2.45 (s, 3H).

Aufarbeitung

  1. concentrationAfter 16 h the reaction was concentrated under vacuum
  2. extractionThe mixture was extracted with Et2O (250 mL)
  3. washthe combined Et2O extracts were washed with brine
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated
  6. customPurification by flash chromatography on silica gel (5-10% (5% NH4OH/MeOH)/CHCl3)

Quellen und Nachweise

ORD-Eintrag
ord-e52bb8a518db433b902508738edab3ad
Quelldatensatz
uspto-grants-2012_05
Patentnummer
US08173646B2

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