Methanol → 3-[4-(Imidazol-1-yl)phenoxy]-1-[(4-methoxynaphth-1-yl)methyl]piperidine

HRID 1270464Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1270464
[N:1]1([C:6]2[CH:18]=[CH:17][C:9]([O:10][CH:11]3[CH2:16][CH2:15][CH2:14][NH:13][CH2:12]3)=[CH:8][CH:7]=2)[CH:5]=[CH:4][N:3]=[CH:2]1.CO.[CH3:21][O:22][C:23]1[C:32]2[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=2)[C:26]([CH:33]=O)=[CH:25][CH:24]=1>C(Cl)Cl>[N:1]1([C:6]2[CH:18]=[CH:17][C:9]([O:10][CH:11]3[CH2:16][CH2:15][CH2:14][N:13]([CH2:33][C:26]4[C:27]5[C:32](=[CH:31][CH:30]=[CH:29][CH:28]=5)[C:23]([O:22][CH3:21])=[CH:24][CH:25]=4)[CH2:12]3)=[CH:8][CH:7]=2)[CH:5]=[CH:4][N:3]=[CH:2]1

Komponenten

5

Edukt 3

HCID 887Methanol2×HCID 852174-Methoxy-1-naphthaldehydeHCID 222600603-[4-(Imidazol-1-yl)phenoxy]piperidine

Produkt 1

HCID 222600553-[4-(Imidazol-1-yl)phenoxy]-1-[(4-methoxynaphth-1-yl)methyl]piperidineAusbeute 10,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a mixture of 3-[4-(imidazol-1-yl)phenoxy]piperidine (308 mg, 1.26 mmol), methanol (6.0 mL) was added 4-methoxy-1-naphthaldehyde (1.25 eq, 298 mg), followed by borane pyridine complex (0.196 mL, 1.25 eq.). The resulting mixture was stirred overnight. The methanol was evaporated, and the residue diluted with ethyl acetate, washed with water and brine. Evaporation of the solvent in vacuo gave a crude product. Flash column chromatography on silical gel with 1–2% methanol in methylene chloride afforded 3-[4-(imidazol-1-yl)phenoxy]-1-[(4-methoxynaphth-1-yl)methyl]piperidine (54 mg), 1H NMR(CDCl3) 8.30 (m, 2), 7.70 (s, 1), 7.50 (m, 2), 7.30 (s, 1), 7.20 (m, 4), 6.90 (m, 2), 6.70 (d, 2), 4.30 (m, 1), 4.00 (s, 3), 3.90 (AB q , 2), 3.10 (m, 1), 2.80 (m, 1), 2.10–2.30 (m, 3), 1.80 (m, 1), 1.40–1.70 (m, 2) ppm.

Aufarbeitung

  1. customThe methanol was evaporated
  2. additionthe residue diluted with ethyl acetate
  3. washwashed with water and brine
  4. customEvaporation of the solvent in vacuo
  5. customgave a crude product

Quellen und Nachweise

ORD-Eintrag
ord-9d25b3e234464a259b48fb1cde04b7ba
Quelldatensatz
uspto-grants-2007_04
Patentnummer
US07202263B2

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