Aluminium lithium hydride → ({3'-[(1-Methyl-4-piperidinyl)methyl]-3-biphenylyl}methyl)amine

HRID 564570Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 564570
Cl.[NH2:2][CH2:3][C:4]1[CH:5]=[C:6]([C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([CH2:16][CH:17]3[CH2:22][CH2:21][N:20]([C:23](OC(C)(C)C)=O)[CH2:19][CH2:18]3)[CH:11]=2)[CH:7]=[CH:8][CH:9]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3]>CCOCC>[CH3:23][N:20]1[CH2:21][CH2:22][CH:17]([CH2:16][C:12]2[CH:11]=[C:10]([C:6]3[CH:7]=[CH:8][CH:9]=[C:4]([CH2:3][NH2:2])[CH:5]=3)[CH:15]=[CH:14][CH:13]=2)[CH2:18][CH2:19]1

Komponenten

4

Edukt 2

HCID 21226445Aluminium lithium hydrideHCID 670057291,1-Dimethylethyl 4-{[3'-(aminomethyl)-3-biphenylyl]methyl}-1-piperidinecarboxylate Hydrochloride

Produkt 1

HCID 57813254({3'-[(1-Methyl-4-piperidinyl)methyl]-3-biphenylyl}methyl)amineAusbeute 68 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3283Diethyl EtherLösungsmittel

Versuchsvorschrift

To 1,1-dimethylethyl 4-{[3′-(aminomethyl)-3-biphenylyl]methyl}-1-piperidinecarboxylate hydrochloride (1.23 g, 2.95 mmol) was added LiAlH4 (5.90 mL, 1N in THF, 5.90 mmol) and the reaction was stirred at room temperature until the was complete per monitoring with LC-MS. The reaction mixture was diluted with Et2O (50 mL) and quenched with Na2CO3 (saturated aqueous), filtered, concentrated and purified with Combiflash chromatograph to afford 0.59 g (68%) of the title compound. LC-MS m/z 295 (M+H)+.

Aufarbeitung

  1. customquenched with Na2CO3 (saturated aqueous)
  2. filtrationfiltered
  3. concentrationconcentrated
  4. custompurified with Combiflash chromatograph

Quellen und Nachweise

ORD-Eintrag
ord-186aeb6004fd4c17bf2c74b668952924
Quelldatensatz
uspto-grants-2011_11
Patentnummer
US08067408B2

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