HCID 13755070, Verbindung → 3-(4-Methoxyphenyl)piperidine

HRID 1507185Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1507185
C([N:8]1[CH2:13][C:12]([C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=2)=[CH:11][CH2:10][CH2:9]1)C1C=CC=CC=1.[H][H]>CO.[Pd]>[CH3:21][O:20][C:17]1[CH:16]=[CH:15][C:14]([CH:12]2[CH2:11][CH2:10][CH2:9][NH:8][CH2:13]2)=[CH:19][CH:18]=1

Komponenten

5

Edukt 2

HCID 13755070HCID 13755070, VerbindungHCID 178418361HCID 178418361, Verbindung

Produkt 1

HCID 129379203-(4-Methoxyphenyl)piperidineAusbeute 69,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 887MethanolLösungsmittel

Versuchsvorschrift

To a solution of 1-benzyl-5-(4-methoxyphenyl)-1,2,3,6-tetrahydropyridine (1.5 g, 5.4 mmol) in 50 mL of methanol was added 10% Pd/C (1.14 g). Hydrogen gas was introduced via balloon and the reaction mixture was stirred overnight at rt. The reaction mixture was then filtered through Celite, and the filter pad was washed with additional methanol (100 mL). The filtrates were combined, and the methanol was evaporated under reduced pressure to give 3-(4-methoxyphenyl)piperidine (950 mg, 3.73 mmol, 69.4% yield). LCMS (Method 107): (ES-API), m/z 192.2 (M+H) RT=1.497 min; 1H NMR (300 MHz, DMSO-d6) δ 7.13 (dt, J=8.5, 2.0 Hz, 2H), 6.84 (dt, J=8.5, 2.2 Hz, 2H), 3.72 (s, 3H), 3.17 (s, 2H), 2.93 (d, J=10.6 Hz, 2H), 2.49-2.39 (m, 1H), 1.81 (d, J=1.9 Hz, 1H), 1.74-1.57 (m, 1H), 1.57-1.40 (m, 2H).

Aufarbeitung

  1. filtrationThe reaction mixture was then filtered through Celite
  2. washthe filter pad was washed with additional methanol (100 mL)
  3. customthe methanol was evaporated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-343bda5298a24223bce1865455728fb5
Quelldatensatz
uspto-grants-2015_12
Patentnummer
US09221796B2

Notizen zur Reaktion

Wird geladen…