Methylamine → Tert-butyl 4-[3-(methylamino)propyl]piperidine-1-carboxylate

HRID 2301192Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2301192
I[CH2:2][CH2:3][CH2:4][CH:5]1[CH2:10][CH2:9][N:8]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:7][CH2:6]1.[CH3:18][NH2:19]>C1COCC1>[CH3:18][NH:19][CH2:2][CH2:3][CH2:4][CH:5]1[CH2:10][CH2:9][N:8]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:7][CH2:6]1

Komponenten

4

Edukt 2

HCID 6329MethylamineHCID 9975355Tert-butyl 4-(3-iodopropyl)piperidine-1-carboxylate

Produkt 1

HCID 18374734Tert-butyl 4-[3-(methylamino)propyl]piperidine-1-carboxylateAusbeute 83 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A solution of 4-(3-iodoprop-1-yl)-1-tert-butoxycarbonyl-piperidine (728 mg, 2.06 mmol,) in 5.0 mL of THF was treated with 5.0 mL of methylamine (70% in water) and the resulting mixture was stirred at rt for 18 h. The mixture was partitioned between diethyl ether (50 mL) and water (50 mL) and the layers were separated. The organic layer was washed with 50 mL of sat'd NaCl, dried and concentrated to afford 457 mg (83%) of the title compound: 1H NMR (500 MHz, CDCl3): δ 1.05-1.68 (19H), 1.47 (s, 9H), 2.45 (s, 3H), 2.56-2.68 (4H), 4.00-4.15 (2H).

Aufarbeitung

  1. customThe mixture was partitioned between diethyl ether (50 mL) and water (50 mL)
  2. customthe layers were separated
  3. washThe organic layer was washed with 50 mL of sat'd NaCl
  4. customdried
  5. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-454fd118935e44be8dfdb918ebb27eb0
Quelldatensatz
uspto-grants-2002_12
Patentnummer
US06498161B1

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