Water → (1-Benzyl-4-phenylpiperidin-4-yl)methanamine

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Reaktionsgleichung

[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH2:7]([N:14]1[CH2:19][CH2:18][C:17]([C:26]#[N:27])([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH2:16][CH2:15]1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.O.[OH-].[Na+]>C1COCC1>[NH2:27][CH2:26][C:17]1([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH2:18][CH2:19][N:14]([CH2:7][C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH2:15][CH2:16]1

Komponenten

Reaktionsbedingungen

Temperatur: 0 °C

Versuchsvorschrift

A suspension of 2.8 g of lithium aluminum hydride in 50 ml of THF is cooled to 0° C. and a solution of 20 g of 1-benzyl-4-cyano-4-phenylpiperidine in 50 ml of THF is added dropwise. The mixture is kept stirring for 1 hour at RT and then heated at 40° C. for 1 hour. The reaction mixture is cooled on an ice bath, and 3 ml of water, 3 ml of a 4N solution of NaOH and 12 ml of water are added successively. The inorganic salts are filtered and the filtrate evaporated under vacuum. The residue is chromatographed on silica H, eluting with the gradient of the DCM/MeOH mixture from (100/3; v/v) to (100/10; v/v). 11 g of the expected product are obtained.

Aufarbeitung

temperatureheated at 40° C. for 1 hour
temperatureThe reaction mixture is cooled on an ice bath
filtrationThe inorganic salts are filtered
customthe filtrate evaporated under vacuum
customThe residue is chromatographed on silica H
washeluting with the gradient of the DCM/MeOH mixture from (100/3; v/v) to (100/10; v/v)

Quellen und Nachweise

ORD-Eintrag: ord-178d0cad4cc04375a2a0ab5afd5a7f55
Quelldatensatz: uspto-grants-2001_09
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US06294537B1

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