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Trifluoroacetic acid → 4-Amino-1-(2-chloropyrimidin-4-yl)-4-methylpiperidine

HRID 234642
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 234642
C(OC([NH:8][C:9]1([CH3:22])[CH2:14][CH2:13][N:12]([C:15]2[CH:20]=[CH:19][N:18]=[C:17]([Cl:21])[N:16]=2)[CH2:11][CH2:10]1)=O)(C)(C)C.C1(OC)C=CC=CC=1.FC(F)(F)C(O)=O.[OH-].[Na+]>C(Cl)Cl>[NH2:8][C:9]1([CH3:22])[CH2:14][CH2:13][N:12]([C:15]2[CH:20]=[CH:19][N:18]=[C:17]([Cl:21])[N:16]=2)[CH2:11][CH2:10]1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 6422Trifluoroacetic acidHCID 7519AnisoleHCID 14798Sodium HydroxideHCID 19694924HCID 19694924, Verbindung

Produkt 1

HCID 196949304-Amino-1-(2-chloropyrimidin-4-yl)-4-methylpiperidine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344
Dichloromethane
Lösungsmittel

Versuchsvorschrift

The procedure described in Example 2 is followed up to the end of step (c). A solution of 6.81 g (0.021 mol) of 4-t-butoxycarbonylamino-1-(2-chloropyrimidin-4-yl)-4-methylpiperidine (step c) in 80 ml of anhydrous methylene chloride is cooled under a nitrogen atmosphere and 16.4 ml of anisole and 83 ml of trifluoroacetic acid are added slowly. The mixture is stirred for 1 hour at room temperature and 80 ml of a 30% solution of NaOH are added slowly. The reaction medium is extracted with methylene chloride and dried over Na2SO4 and the solvent and the anisole are evaporated off under reduced pressure to give 4-amino-1-(2- chloropyrimidin-4-yl)-4-methylpiperidine as the base, which is treated with maleic acid in an ethanol/ethyl ether mixture. The maleate obtained in this way is isolated by filtration (yield 65%, m.p. 125°-126° C.).

Aufarbeitung

  1. extractionThe reaction medium is extracted with methylene chloride
  2. dry with materialdried over Na2SO4
  3. customthe solvent and the anisole are evaporated off under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-3f9edbb5f6b64dddab7450886a852fd9
Quelldatensatz
uspto-grants-1997_01
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05595994

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