Triphenylphosphine → 4-[4-[2-(1-methyl-1H-pyrazol-5-yl)ethoxy]phenyl]piperidine

HRID 1675146

Reaktionsgleichung

Reaktionsgleichung von HRID 1675146
CC(OC(/N=N/C(OC(C)C)=O)=O)C.[NH:15]1[CH2:20][CH2:19][CH:18]([C:21]2[CH:26]=[CH:25][C:24]([OH:27])=[CH:23][CH:22]=2)[CH2:17][CH2:16]1.[CH3:28][N:29]1[C:33]([CH2:34][CH2:35]O)=[CH:32][CH:31]=[N:30]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C(Cl)Cl>[CH3:28][N:29]1[C:33]([CH2:34][CH2:35][O:27][C:24]2[CH:23]=[CH:22][C:21]([CH:18]3[CH2:19][CH2:20][NH:15][CH2:16][CH2:17]3)=[CH:26][CH:25]=2)=[CH:32][CH:31]=[N:30]1

Komponenten

6

Edukt 4

HCID 11776TriphenylphosphineHCID 5363146Diisopropyl azodicarboxylateHCID 105115114-Piperidin-4-ylphenolHCID 218324192-(1-methyl-1H-pyrazol-5-yl)ethan-1-ol2×

Produkt 1

HCID 673403084-[4-[2-(1-methyl-1H-pyrazol-5-yl)ethoxy]phenyl]piperidineAusbeute 99,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
22 °C

Versuchsvorschrift

DIAD (64.8 μl, 0.33 mmol) was added to 4-(piperidin-4-yl)phenol (CAS 263139-27-1, 53 mg, 0.30 mmol), 2-(1-methyl-1H-pyrazol-5-yl)ethanol (obtained as described in PCT Int. Appl. WO 2007017222, Intermediate 1) (37.7 mg, 0.30 mmol) and triphenylphosphine (86 mg, 0.33 mmol) in DCM (3 mL) at 20° C. under nitrogen. The resulting mixture was stirred at 22° C. for 3 days. The reaction mixture was purified by ion exchange chromatography, using an SCX column. The desired product was eluted from the column using 7M ammonia in methanol and pure fractions were evaporated to dryness to afford 4-[4-[2-(1-methyl-1H-pyrazol-5-yl)ethoxy]phenyl]piperidine (85 mg, 96%) as a yellow oil.

Aufarbeitung

  1. customThe reaction mixture was purified by ion exchange chromatography
  2. washThe desired product was eluted from the column
  3. customwere evaporated to dryness

Quellen und Nachweise

ORD-Eintrag
ord-64bc66898c944875a16910785de0ea9b
Quelldatensatz
uspto-grants-2011_08
Patentnummer
US08003649B2

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