1-Methyl-4-[(4-nitrophenoxy)methyl]piperidine → 4-((1-Methyl-4-piperidinyl)methoxy)benzenamine

HRID 1366155

Reaktionsgleichung

Reaktionsgleichung von HRID 1366155
N1(CCOC2C=CC(NC3C4N(C=CN=4)C(C4C=NNC=4)=CN=3)=CC=2)CCOCC1.[CH3:31][N:32]1[CH2:37][CH2:36][CH:35]([CH2:38][O:39][C:40]2[CH:45]=[CH:44][C:43]([N+:46]([O-])=O)=[CH:42][CH:41]=2)[CH2:34][CH2:33]1>C(O)C.[OH-].[Pd+2].[OH-]>[CH3:31][N:32]1[CH2:37][CH2:36][CH:35]([CH2:38][O:39][C:40]2[CH:41]=[CH:42][C:43]([NH2:46])=[CH:44][CH:45]=2)[CH2:34][CH2:33]1

Komponenten

5

Edukt 2

HCID 115940001-Methyl-4-[(4-nitrophenoxy)methyl]piperidineHCID 59023066[4-(2-Morpholin-4-yl-ethoxy)-phenyl]-[5-(1H-pyrazol-4-yl)-imidazo[1,2-a]pyrazin-8-yl]amine

Produkt 1

HCID 115647984-((1-Methyl-4-piperidinyl)methoxy)benzenamine

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 9942167Palladium hydroxideKatalysatorHCID 702EthanolLösungsmittel

Versuchsvorschrift

In the same way as described for Compound 150, step 1, using 1-methyl-4-(4-nitro-phenoxymethyl)-piperidine (0.65 g, 2.6 mmol) in ethanol (40 mL) and palladium hydroxide (0.182 g, 0.26 mmol). Filtration over Celite 521 and evaporation gave a red oil that was purified by silica gel column chromatography eluting with DCM and a 80:20 mixture DCM:MeOH. The title compound was obtained as a white solid (0.402 g, 70%). 1H-NMR (400 MHz, CDCl3) δ (ppm) 1.30-1.51 (2H, m), 1.65-1.88 (3H, m), 1.89-2.09 (2H, t), 2.29 (3H, s), 2.90 (2H, d,), 3.45 (2H, br s), 3.73 (2H, d), 6.67 (2H, d), 6.75 (2H, d).

Aufarbeitung

  1. filtrationFiltration
  2. customover Celite 521 and evaporation
  3. customgave a red oil that
  4. customwas purified by silica gel column chromatography
  5. washeluting with DCM

Quellen und Nachweise

ORD-Eintrag
ord-8fa6a4196a91417b84d469b868152aa7
Quelldatensatz
uspto-grants-2011_02
Patentnummer
US07893058B2

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