Propionyl chloride → N-(1-Boc-piperidin-3-ylmethyl)-N-phenyl-propionamide

HRID 479785

Reaktionsgleichung

Reaktionsgleichung von HRID 479785
[C:1]([N:8]1[CH2:13][CH2:12][CH2:11][CH:10]([CH2:14][NH:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH2:9]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].C(N(CC)C(C)C)(C)C.[C:31](Cl)(=[O:34])[CH2:32][CH3:33]>C(Cl)Cl>[C:1]([N:8]1[CH2:13][CH2:12][CH2:11][CH:10]([CH2:14][N:15]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:31](=[O:34])[CH2:32][CH3:33])[CH2:9]1)([O:3][C:4]([CH3:6])([CH3:7])[CH3:5])=[O:2]

Komponenten

5

Edukt 3

HCID 62324Propionyl chlorideHCID 81531DiisopropylethylamineHCID 12972131N-(1-Boc-piperidin-3-ylmethyl)aniline

Produkt 1

HCID 12991578N-(1-Boc-piperidin-3-ylmethyl)-N-phenyl-propionamideAusbeute 82,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of N-(1-Boc-piperidin-3-ylmethyl)-aniline 4 (4.60 g, 15.8 mmol) and N,N-diisopropylethylamine (1.40 mL, 15.8 mmol) in 25 mL of dry methylene chloride was added propionyl chloride (1.40 mL, 15.8 mmol) dropwise at 0° C. After being stirred at room temperature overnight, the reaction mixture was quenched with 30 mL of H2O and extracted with ethyl acetate (3×100 mL). The extracts were combined and washed with aqueous HCl (5%, 20 mL), NaHCO3 (sat., 2×30 mL), brine (50 mL), and dried over anhydrous sodium sulfate. After the solvent was removed, the remaining oily residue was purified by a flash column chromatography (silica gel, hexane:ethyl acetate) to afford N-(1-Boc-piperidin-3-ylmethyl)-N-phenyl-propionamide 5 as a colorless oil (4.50 g, 82%). IR (film, cm−1) 2975, 2934, 2854, 1690, 1663, 1591, 1496, 1422, 1402, 1365, 1265, 1242, 1176, 1149, 1038, 962,775, 702; 1H NMR (CDCl3, ppm) 7.44-7.22 (m, 5H), 4.09-3.22 (m, 4H), 2.80-2.09 (m, 2H), 2.06 (q, 2H, J=7.5 Hz), 1.75-1.19 (m, 5H), 1.48(s, overlap, 9H), 1.06 (t, 3H, J=7.5 Hz).

Aufarbeitung

  1. customthe reaction mixture was quenched with 30 mL of H2O
  2. extractionextracted with ethyl acetate (3×100 mL)
  3. washwashed with aqueous HCl (5%, 20 mL), NaHCO3 (sat., 2×30 mL), brine (50 mL)
  4. dry with materialdried over anhydrous sodium sulfate
  5. customAfter the solvent was removed
  6. customthe remaining oily residue was purified by a flash column chromatography (silica gel, hexane:ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-f4c199a21bbc48189c330caf33dd4bbe
Quelldatensatz
uspto-grants-2003_11
Patentnummer
US06645980B1

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