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

HRID 1710551Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1710551
[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-5cabe43a12ce45d7b2fc778fb5c3f716
Quelldatensatz
uspto-grants-2010_09
Patentnummer
US07790716B2

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