Pseudoephedrine → N-(2-hydroxy-1-methyl-2-phenylethyl)-N-methyl hexanamide

HRID 376018

Reaktionsgleichung

Reaktionsgleichung von HRID 376018
[CH3:1][C@H:2]([NH:11][CH3:12])[C@@H:3]([OH:10])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[C:13](OC(=O)CCCCC)(=O)[CH2:14]CCCC.[O:28]1[CH2:32][CH2:31][CH2:30][CH2:29]1>>[OH:10][CH:3]([C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1)[CH:2]([N:11]([CH3:12])[C:32](=[O:28])[CH2:31][CH2:30][CH2:29][CH2:13][CH3:14])[CH3:1]

Komponenten

4

Edukt 3

HCID 7028PseudoephedrineHCID 8028Tetrahydrofuran2×HCID 74918Hexanoic anhydride

Produkt 1

HCID 54856796N-(2-hydroxy-1-methyl-2-phenylethyl)-N-methyl hexanamideAusbeute 91 %

Reaktionsbedingungen

Temperatur
23 °C

Versuchsvorschrift

In a dry 2 L round-bottomed flask equipped with a magnetic stirrer was added (+)-pseudoephedrine (40.0 g, 242.06 mmol, 1.0 equiv) and tetrahydrofuran (500 mL), and the mixture was stirred in a 23° C. water bath. Hexanoic anhydride (55.51 g, 259 mmol, 1.07 equiv) was added via cannula over a 10 minute interval, and transfer was quantitated with an additional portion of tetrahydrofuran (10 mL). After 25 minutes, the reaction was quenched with saturated sodium bicarbonate (300 mL). Volatile components were removed under reduced pressure, and the residue was extracted from water (500 mL) with ethyl acetate (3×250 mL). The organic extracts were dried over sodium sulfate, and after removal of the solvent under reduced pressure, a white solid was obtained, which was recrystallized from 1:1 ether/hexanes (200 mL) to afford the hexanamide as white crystals (58.2 g, 91% yield): mp 62°-63° C.; 1H NMR (300 MHz, C 6D6) δ7.0-7.4 (m, 5H), 4.9 (br, 1H), 4.52 (d, 1H, J=6.9 Hz), 4.14 (m, 1H), 3.77 (m, 1H), 2.79 (s, 3H), 2.42 (m, 2H), 2.13 (s, 3H), 1.83 (m, 2H), 1.59 (qn, 2H, J=7.6 Hz), 1.1-1.4 (m, 4H), 0.99 (d, 3H, J=7.0 Hz), 0.86 (t, 3H, J=7.0 Hz), 0.59 (d, 3H, J=6.8 Hz); 13C NMR (75.5 MHz, CDCl3) δ175.2, 174.2, 142.3, 141.6, 128.3, 128.0, 127.8, 127.3, 126.7, 126.2, 76.1, 75.1, 58.2, 57.0, 34.1, 33.4, 32.4, 31.5, 31.3, 26.6, 24.9, 24.5, 22.31, 22.29, 15.2, 14.2, 13.82, 13.79; FTIR (neat film) cm-1 3378 (br, m), 2956 (m), 2931 (m), 2871 (m), 1618 (s), 1453 (m), 1406 (m), 1051 (m), 701 (m); HRMS (FAB) Calcd for C16H26N02 (MH+): 264.1965. Found: 264.1966.

Aufarbeitung

  1. customIn a dry 2 L round-bottomed flask equipped with a magnetic stirrer
  2. customthe reaction was quenched with saturated sodium bicarbonate (300 mL)
  3. customVolatile components were removed under reduced pressure
  4. extractionthe residue was extracted from water (500 mL) with ethyl acetate (3×250 mL)
  5. dry with materialThe organic extracts were dried over sodium sulfate
  6. customafter removal of the solvent under reduced pressure
  7. customa white solid was obtained
  8. customwhich was recrystallized from 1:1 ether/hexanes (200 mL)

Quellen und Nachweise

ORD-Eintrag
ord-d860696d3f844abfa70eb9235d0bf5fc
Quelldatensatz
uspto-grants-1996_01
Patentnummer
US05488131

Verknüpfte Notizen

Wird geladen…