N-Methylbutylamine → Methyl 5-{[butyl(methyl)amino]methyl}thiophene-2-carboxylate

HRID 14108

Reaktionsgleichung

Reaktionsgleichung von HRID 14108
Br[CH2:2][C:3]1[S:7][C:6]([C:8]([O:10][CH3:11])=[O:9])=[CH:5][CH:4]=1.[CH3:12][NH:13][CH2:14][CH2:15][CH2:16][CH3:17]>CC(C)=O>[CH2:14]([N:13]([CH2:2][C:3]1[S:7][C:6]([C:8]([O:10][CH3:11])=[O:9])=[CH:5][CH:4]=1)[CH3:12])[CH2:15][CH2:16][CH3:17]

Komponenten

4

Edukt 2

HCID 8068N-MethylbutylamineHCID 11424851Methyl 5-(bromomethyl)thiophene-2-carboxylate

Produkt 1

HCID 21086213Methyl 5-{[butyl(methyl)amino]methyl}thiophene-2-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 180AcetoneLösungsmittel

Versuchsvorschrift

To a solution of methyl 5-(bromomethyl)thiophene-2-carboxylate (350 mg, 1.49 mmol) in dry acetone (6.0 mL) is added N-methylbutylamine (533 μL, 4.47 mmol) and the solution stirred at room temperature overnight. The reaction is then concentrated under reduced pressure, redissolved in methylene chloride, washed with saturated sodium bicarbonate, water, and brine. The organic layer is then dried (sodium sulfate), filtered, and concentrated under reduced pressure to yield the title compound in pure form. 1H NMR (300 MHz, CDCl3) δ 7.65 (d, J=3 Hz, 1H), 6.88 (d, J=3 Hz, 1H), 3.86 (s, 3H), 3.69 (s, 2H), 2.41-2.36 (m, 2H), 2.25 (s, 3H), 1.53-1.43 (m, 2H), 1.34-1.25 (m, 2H), 0.91 (t, J=7 Hz, 3H).

Aufarbeitung

  1. concentrationThe reaction is then concentrated under reduced pressure
  2. dissolutionredissolved in methylene chloride
  3. washwashed with saturated sodium bicarbonate, water, and brine
  4. dry with materialThe organic layer is then dried (sodium sulfate)
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-9aaf626347dc44ce96bbc4c487c5589d
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07727997B2

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