Dimethylamine → 1-(7-Fluoro-1H-indol-3-yl)-N,N-dimethylmethanamine

HRID 1098612

Reaktionsgleichung

Reaktionsgleichung von HRID 1098612
C=O.[CH3:3][NH:4][CH3:5].[F:6][C:7]1[CH:8]=[CH:9][CH:10]=[C:11]2[C:15]=1[NH:14][CH:13]=[CH:12]2.[C:16]([O-])([O-])=O.[K+].[K+].[OH-].[Na+]>C(O)(=O)C>[F:6][C:7]1[CH:8]=[CH:9][CH:10]=[C:11]2[C:5]=1[NH:4][CH:3]=[C:12]2[CH2:13][N:14]([CH3:15])[CH3:16]

Komponenten

7

Edukt 5

HCID 674DimethylamineHCID 712FormaldehydeHCID 11430Potassium CarbonateHCID 14798Sodium HydroxideHCID 27745047-Fluoro-1H-indole

Produkt 1

HCID 249051291-(7-Fluoro-1H-indol-3-yl)-N,N-dimethylmethanamineAusbeute 74 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 176Acetic AcidLösungsmittel

Versuchsvorschrift

To a mixture of acetic acid (13.6 mL) and formaldehyde (0.340 mL, 4.5 mmol, 37% solution) under argon was added dimethyl amine (2.05 mL, 16.3 mmol., 40% solution). The reaction mixture was stirred for 10 min and then treated with 7-fluoroindole (540 mg, 4.0 mmol.). The resulting mixture was stirred at room temperature for ˜16 h. The reaction mixture was first neutralized with K2CO3 and then basified with NaOH (2N), and then extracted in ethyl acetate, washed with water, dried, and concentrated. Solid obtained was recrystallized from ethyl acetate and hexane to give (7-Fluoro-1H-indol-3-ylmethyl)dimethylamine (570 mg, 74%): mp 133-137° C., 1H NMR (500 MHz, CDCl3): 2.31 (s, 6H), 3.62 (s, 2H), 6.88-6.92 (dd, J=8.0 and 8.0 Hz, 1H), 7.00-7.04 (m, 1H), 7.16 (d, J=2.5 Hz, 1H), 7.46 (d, J=8.0 Hz, 1H), 8.34 (s, 1H).

Aufarbeitung

  1. stirringThe resulting mixture was stirred at room temperature for ˜16 h
  2. extractionextracted in ethyl acetate
  3. washwashed with water
  4. customdried
  5. concentrationconcentrated
  6. customSolid obtained
  7. customwas recrystallized from ethyl acetate and hexane

Quellen und Nachweise

ORD-Eintrag
ord-554ffaa698dc49f989831814a088d201
Quelldatensatz
uspto-grants-2012_03
Patentnummer
US08143300B2

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