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

HRID 348900

Reaction equation

HRID 348900 reaction equation
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]

Participants

4

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

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)

Workup

  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

Sources & evidence

ORD record
ord-218df0caef1643e8b4cf8d84d25386ac
Source dataset
uspto-grants-2007_02
Patent number
US07176242B2

Linked notes

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