1-Benzyl-4-piperidone → HCID 58772035, Verbindung

HRID 1361508Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1361508
Br[C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[O:9][CH3:10].[Li]CCCC.[CH2:16]([N:23]1[CH2:28][CH2:27][C:26](=[O:29])[CH2:25][CH2:24]1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>C1COCC1>[CH2:16]([N:23]1[CH2:28][CH2:27][C:26]([C:2]2[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=2[O:9][CH3:10])([OH:29])[CH2:25][CH2:24]1)[C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1

Komponenten

5

Edukt 3

HCID 192201-Benzyl-4-piperidoneHCID 5219352-Bromo-4-chloroanisoleHCID 178418339Butyllithium

Produkt 1

HCID 58772035HCID 58772035, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
-78 °C

Versuchsvorschrift

To a solution of 2-bromo-4-chloroanisole (1a, 51 g, 0.23 mol) in THF (500 mL) was added dropwise n-BuLi (2.5 M in hexane, 138 mL, 0.345 mol) at −78° C. under nitrogen atmosphere. After being stirred at −78° C. for 1 h, 1-benzyl-piperidin-4-one (42 g, 0.22 mol) was added dropwise. After addition, the mixture was stirred at this temperature for 1 h, and then warmed to room temperature. The reaction was quenched with saturated NH4Cl (300 mL) and the separated aqueous layer was extracted with ethyl acetate (150 mL×3). The combined extracts were washed with water and brine, dried over Na2SO4, concentrated to dryness. The residue was purified by silica gel column to obtain 1-benzyl-4-(5-chloro-2-methoxy-phenyl)-piperidin-4-ol 1b as a white solid. 1H NMR (CDCl3): δ 7.37-7.24 (m, 6H), 7.21 (q, J1=8.8 Hz, J2=2.8 Hz, 1H), 6.85 (d, J=8.8 Hz, 1H), 3.88 (s, 3H), 3.80 (s, 1H), 3.59 (s, 2, H), 2.77-2.74 (m, 2, H), 2.59-2.54 (t, 2H), 2.13-2.06 (m, 2H), 2.00-1.96 (m, 2H).

Aufarbeitung

  1. additionAfter addition
  2. stirringthe mixture was stirred at this temperature for 1 h
  3. temperaturewarmed to room temperature
  4. customThe reaction was quenched with saturated NH4Cl (300 mL)
  5. extractionthe separated aqueous layer was extracted with ethyl acetate (150 mL×3)
  6. washThe combined extracts were washed with water and brine
  7. dry with materialdried over Na2SO4
  8. concentrationconcentrated to dryness
  9. customThe residue was purified by silica gel column

Quellen und Nachweise

ORD-Eintrag
ord-5f381344ca6a4df9a8c762a4f23702b6
Quelldatensatz
uspto-grants-2011_02
Patentnummer
US07880007B2

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