Methylamine → N-Methyl-1H-indole-3-methanamine

HRID 1297364

Reaktionsgleichung

Reaktionsgleichung von HRID 1297364
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([CH:10]=O)=[CH:2]1.[CH3:12][NH2:13].[BH4-].[Na+]>CO>[CH3:12][NH:13][CH2:10][C:3]1[C:4]2[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=2)[NH:1][CH:2]=1

Komponenten

5

Edukt 3

HCID 6329MethylamineHCID 10256Indole-3-CarboxaldehydeHCID 4311764Sodium borohydride

Produkt 1

HCID 96388N-Methyl-1H-indole-3-methanamine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel2×

Versuchsvorschrift

To a solution of indole-3-carboxaldehyde (5.4 g, 34.1 mmole) in MeOH (30 mL) was added a solution of 2.0 M CH3NH2 in MeOH (51.3 mL, 102.6 mmole). The reaction was stirred at RT overnight, then was concentrated to a light yellow oil. This oil was dissolved in EtOH (40 mL), and NaBH4 (1.3 g, 34.1 mmole) was added. After 16 hrs the reaction was concentrated to a slurry and dissolved in 10% Na2CO3(100 mL). The aqueous solution was extracted with EtOAc (2×200 mL) and the combined organic fractions were dried over Na2SO4 and concentrated. Drying in high vacuum left the title compound (5.2 g, 94%) as a faintly yellow oil: MS (ES) m/e 161 (M+H)+.

Aufarbeitung

  1. concentrationwas concentrated to a light yellow oil
  2. dissolutionThis oil was dissolved in EtOH (40 mL)
  3. concentrationAfter 16 hrs the reaction was concentrated to a slurry
  4. dissolutiondissolved in 10% Na2CO3(100 mL)
  5. extractionThe aqueous solution was extracted with EtOAc (2×200 mL)
  6. dry with materialthe combined organic fractions were dried over Na2SO4
  7. concentrationconcentrated
  8. customDrying in high vacuum
  9. waitleft the title compound (5.2 g, 94%) as a faintly yellow oil

Quellen und Nachweise

ORD-Eintrag
ord-7ff0402a46c5493aa972c6b7737ad95f
Quelldatensatz
uspto-grants-2007_07
Patentnummer
US07250424B2

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