Aluminium lithium hydride → 4-(4-Bromophenyl)-4-(4-chlorophenyl)-1-methylpiperidine

HRID 924708Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 924708
C(O[C:4]([N:6]1[CH2:11][CH2:10][C:9]([C:19]2[CH:24]=[CH:23][C:22]([Br:25])=[CH:21][CH:20]=2)([C:12]2[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][CH:13]=2)[CH2:8][CH2:7]1)=O)C.[H-].[Al+3].[Li+].[H-].[H-].[H-]>O1CCCC1>[Br:25][C:22]1[CH:23]=[CH:24][C:19]([C:9]2([C:12]3[CH:13]=[CH:14][C:15]([Cl:18])=[CH:16][CH:17]=3)[CH2:10][CH2:11][N:6]([CH3:4])[CH2:7][CH2:8]2)=[CH:20][CH:21]=1

Komponenten

4

Edukt 2

HCID 21226445Aluminium lithium hydrideHCID 59331961HCID 59331961, Verbindung

Produkt 1

HCID 576913994-(4-Bromophenyl)-4-(4-chlorophenyl)-1-methylpiperidineAusbeute 100,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

Under a nitrogen atmosphere 4-(4-Bromo-phenyl)-4-(4-chloro-phenyl)-piperidine-1-carboxylic acid ethyl ester (0.28 g, 0.66 mmol) and lithium aluminum hydride (0.051 g) were suspended in tetrahydrofuran (5 ml) and stirred for 2 hours. The reaction mixture was quenched with addition of water, solvent removed under reduced pressure, the residue was partitioned between ethyl acetate and 2N NaOH. The organic layer was washed with brine, dried (MgSO4), filtered and concentrated to afford the desired product (0.241 g, 99% yield). LC/MS: (PS-B3) Rt 3.78 [M+H]+ 363.95, 365.73.

Aufarbeitung

  1. customThe reaction mixture was quenched with addition of water, solvent
  2. customremoved under reduced pressure
  3. customthe residue was partitioned between ethyl acetate and 2N NaOH
  4. washThe organic layer was washed with brine
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-11e89b241f914f9db9a223b73cbd140c
Quelldatensatz
uspto-grants-2016_03
Patentnummer
US09283226B2

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