Acrylonitrile → 1-(3-Aminopropyl)-4-[2-(1,5-di-[3,3-dimethylbicyclo[2.2.1]hept-2-yl]-3-pentylamino)ethyl]piperidine

HRID 1415332

Reaktionsgleichung

Reaktionsgleichung von HRID 1415332
[NH2:1][CH2:2][CH2:3][CH:4]1[CH2:9][CH2:8][NH:7][CH2:6][CH2:5]1.[CH3:10][C:11]1([CH3:33])[CH:16]2[CH2:17][CH:13]([CH2:14][CH2:15]2)[CH:12]1[CH2:18][CH2:19][C:20](=O)[CH2:21][CH2:22][CH:23]1[C:28]([CH3:30])([CH3:29])[CH:27]2[CH2:31][CH:24]1[CH2:25][CH2:26]2.[C:34](#[N:37])[CH:35]=[CH2:36]>>[NH2:37][CH2:34][CH2:35][CH2:36][N:7]1[CH2:8][CH2:9][CH:4]([CH2:3][CH2:2][NH:1][CH:20]([CH2:21][CH2:22][CH:23]2[C:28]([CH3:29])([CH3:30])[CH:27]3[CH2:31][CH:24]2[CH2:25][CH2:26]3)[CH2:19][CH2:18][CH:12]2[C:11]([CH3:33])([CH3:10])[CH:16]3[CH2:15][CH:14]2[CH2:13][CH2:17]3)[CH2:5][CH2:6]1

Komponenten

4

Edukt 3

HCID 7855AcrylonitrileHCID 15126024-PiperidineethanamineHCID 213328461,5-Di-(3,3-dimethylnorborn-2-yl)-3-pentanone

Produkt 1

HCID 214839691-(3-Aminopropyl)-4-[2-(1,5-di-[3,3-dimethylbicyclo[2.2.1]hept-2-yl]-3-pentylamino)ethyl]piperidine

Versuchsvorschrift

As an alternative to obtaining a mixture of Schiff bases VI and VI(a) or VI(b), the reaction can be conducted stepwise. For example, 4-(2-aminoethyl)piperidine may be converted to a Schiff base with 1,5-di-[3,3-dimethylbicyclo[2.2.1]hept-2-yl]pentan-3-one, catalytically reduced, the ring nitrogen selectively cyanoethylated with acrylonitrile, followed by catalytic hydrogenation to furnish 1-(3-aminopropyl)-4-[2-(1,5-di-[3,3-dimethylbicyclo[2.2.1]hept-2-yl]-3-pentylamino)ethyl]piperidine.

Aufarbeitung

  1. customAs an alternative to obtaining
  2. customthe reaction

Quellen und Nachweise

ORD-Eintrag
ord-71023bb448a74992ad683619ac9ef9d1
Quelldatensatz
uspto-grants-1977_01
Patentnummer
US04003934

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