Ammonia → 4-(3-Aminopropyl)-4-cyclohexylpiperidine-1-carboxylic acid tert-butyl ester

HRID 1795175Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1795175
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C:11]([CH:20]=[CH:21][C:22]#[N:23])([CH:14]2[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].N>CO.[Ni]>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C:11]([CH2:20][CH2:21][CH2:22][NH2:23])([CH:14]2[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19]2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Komponenten

5

Edukt 2

HCID 222AmmoniaHCID 695970864-(2-Cyanovinyl)-4-cyclohexylpiperidine-1-carboxylic acid tert-butyl ester

Produkt 1

HCID 210237744-(3-Aminopropyl)-4-cyclohexylpiperidine-1-carboxylic acid tert-butyl ester

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 935NickelKatalysatorHCID 887MethanolLösungsmittel

Versuchsvorschrift

To a solution of 4-(2-cyanovinyl)-4-cyclohexylpiperidine-1-carboxylic acid tert-butyl ester, 14, (800 mg, 2.35 mmol) in MeOH (33 mL) is added ammonia (16 mL) and Raney Ni (50 mg). The reaction mixture is degassed with nitrogen, purged with hydrogen gas and shaken under an atmosphere of hydrogen (45 psi) on a standard hydrogenation apparatus at room temperature for 6 hours. The reaction solution is filtered to remove the catalyst and the solvent removed in vacuo to afford the desired product was obtained as a colorless, sticky oil in quantitative yield.

Aufarbeitung

  1. customThe reaction mixture is degassed with nitrogen
  2. custompurged with hydrogen gas
  3. filtrationThe reaction solution is filtered
  4. customto remove the catalyst
  5. customthe solvent removed in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-6d37f3a415b64af89315f71cd3701724
Quelldatensatz
uspto-grants-2006_04
Patentnummer
US07026335B2

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