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

HRID 1361512Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1361512
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

Versuchsvorschrift

To a solution of 2-bromo-4-chloro-1-methoxybenzene (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. at nitrogen atmosphere. After being stirred at this temperature for 1 h, 1-benzyl-piperidin-4-one (42 g, 0.22 mol) was added dropwise. After addition, the mixture was stirred at −78° C. for 1 h, and then warmed to room temperature. The reaction was quenched with NH4Cl (Sat. aq., 300 mL), and the separated aqueous layer was extracted with ethyl acetate (150 mL×3). The combined organic layer was 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 4b as white powder product. 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 −78° C. for 1 h
  3. customThe reaction was quenched with NH4Cl (Sat. aq., 300 mL)
  4. extractionthe separated aqueous layer was extracted with ethyl acetate (150 mL×3)
  5. washThe combined organic layer was washed with water and brine
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated to dryness
  8. customThe residue was purified by silica gel column

Quellen und Nachweise

ORD-Eintrag
ord-973a607542da40de8e81f0f28046a167
Quelldatensatz
uspto-grants-2011_02
Patentnummer
US07880007B2

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