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Bicyclo[2.2.2]octan-1-amine hydrochloride → 4-Aminobicyclo(2.2.2)octane

HRID 539606
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 539606
CC1(C)C(C)(C)OC(OC2C=CC([N+]([O-])=O)=CC=2)=NS1(=O)=O.Cl.[NH2:24][C:25]12[CH2:32][CH2:31][CH:28]([CH2:29][CH2:30]1)[CH2:27][CH2:26]2>ClCCl.C(N(CC)C(C)C)(C)C>[NH2:24][C:25]12[CH2:32][CH2:31][CH:28]([CH2:29][CH2:30]1)[CH2:27][CH2:26]2
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Komponenten

5

Edukt 2

HCID 13182386Bicyclo[2.2.2]octan-1-amine hydrochlorideHCID 718136815,5,6,6-Tetramethyl-2-(4-nitrophenoxy)-5,6-dihydro-1,4,3-oxathiazine 4,4-dioxide

Produkt 1

HCID 5502144-Aminobicyclo(2.2.2)octaneAusbeute 131,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittelHCID 81531Diisopropylethylamine
Lösungsmittel

Versuchsvorschrift

300 mg of 5,5,6,6-tetramethyl-2-(4-nitrophenoxy)-5,6-dihydro-1,4,3-oxathiazine 4,4-dioxide and 163 mg of 1-aminobicyclo[2.2.2]octane hydrochloride were dissolved in a mixture of 5 ml of dichloromethane and 0.38 ml of N,N-diisopropylethylamine, and the mixture was stirred at room temperature for 72 hours. Subsequently, the reaction solution was concentrated by rotary evaporation and the residue was purified in a purification laboratory by means of preparative HPLC. After lyophilization of the product-containing fractions, the product (166 mg) was thus obtained with a molecular weight of 314.5 g/mol (C15H26N2O3S); MS (ESI): m/e=315 (M+H+).

Aufarbeitung

  1. concentrationSubsequently, the reaction solution was concentrated by rotary evaporation
  2. customthe residue was purified in a purification laboratory by means of preparative HPLC

Quellen und Nachweise

ORD-Eintrag
ord-082cb8e1755b4ea7809d1ee5dcab8bf9
Quelldatensatz
uspto-grants-2014_10
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08871758B2

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