Ethyl Acetate → Butyl 4-((3,4-diaminophenoxy)methyl)piperidine-1-carboxylate

HRID 415101Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 415101
[NH2:1][C:2]1[CH:22]=[CH:21][C:5]([O:6][CH2:7][CH:8]2[CH2:13][CH2:12][N:11]([C:14]([O:16][C:17]([CH3:20])(C)C)=[O:15])[CH2:10][CH2:9]2)=[CH:4][C:3]=1[N+:23]([O-])=O.[H][H].[C:28](OCC)(=O)[CH3:29]>CO.[Pd]>[NH2:23][C:3]1[CH:4]=[C:5]([CH:21]=[CH:22][C:2]=1[NH2:1])[O:6][CH2:7][CH:8]1[CH2:9][CH2:10][N:11]([C:14]([O:16][CH2:17][CH2:20][CH2:28][CH3:29])=[O:15])[CH2:12][CH2:13]1

Komponenten

6

Edukt 3

HCID 8857Ethyl AcetateHCID 59349493Tert-butyl 4-((4-amino-3-nitrophenoxy)methyl)piperidine-1-carboxylateHCID 178418361HCID 178418361, Verbindung

Produkt 1

HCID 86642035Butyl 4-((3,4-diaminophenoxy)methyl)piperidine-1-carboxylateAusbeute 100 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 887MethanolLösungsmittel

Versuchsvorschrift

tert-Butyl 4-((4-amino-3-nitrophenoxy)methyl)piperidine-1-carboxylate (3.58 g, 10.18 mmoles,) was dissolved in ethyl acetate (60 ml) and methanol (40 ml). The solution was treated with 600 mg of 10% palladium on carbon (50% water w/w). The slurry was then shaken on a Parr hydrogenator and treated with a 40 psi of hydrogen gas, at room temperature. After 16 hours, the slurry was filtered through a plug of Celite, which was subsequently washed with ethyl acetate (50 ml) and methanol (50 ml). The resulting filtrate was then evaporated at reduced pressure to give 3.42 g of tent-butyl 4-((3,4-diaminophenoxy)methyl)piperidine-1-carboxylate (100% yield). The material was used in the next step without any further purification. 1H-NMR (400 MHz, DMSO-d6) δ 8.40 (s, 1H), 7.49 (d, 1H), 7.24 (d, 1H), 5.32 (br s, 4H), 3.82 (d, 2H), 3.65 (m, 2H), 2.40 (s, 3H), 1.76 (m, 1H), 1.54 (m, 2H), 1.38 (s, 9H), 0.98 (m, 2H). MS (EI): 322 (MH+).

Aufarbeitung

  1. filtrationthe slurry was filtered through a plug of Celite, which
  2. washwas subsequently washed with ethyl acetate (50 ml) and methanol (50 ml)
  3. customThe resulting filtrate was then evaporated at reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-fc327245eb1942d094c51e7373babaab
Quelldatensatz
uspto-grants-2012_01
Patentnummer
US08088767B2

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