Water → Ethyl 4-[[4-dimethylamino-2-pyrimidinyl]methylamino]-1-piperidinecarboxylate

HRID 1274996

Reaktionsgleichung

Reaktionsgleichung von HRID 1274996
[CH3:1][NH:2][CH:3]1[CH2:8][CH2:7][N:6]([C:9]([O:11][CH2:12][CH3:13])=[O:10])[CH2:5][CH2:4]1.Cl[C:15]1[N:20]=[C:19]([N:21]([CH3:23])[CH3:22])[CH:18]=[CH:17][N:16]=1.O>ClC(Cl)Cl>[CH3:22][N:21]([CH3:23])[C:19]1[CH:18]=[CH:17][N:16]=[C:15]([CH2:1][NH:2][CH:3]2[CH2:8][CH2:7][N:6]([C:9]([O:11][CH2:12][CH3:13])=[O:10])[CH2:5][CH2:4]2)[N:20]=1

Komponenten

5

Edukt 3

HCID 962WaterHCID 959752-Chloro-N,N-dimethylpyrimidin-4-amineHCID 11063140Ethyl 4-(Methylamino)Piperidine-1-Carboxylate

Produkt 1

HCID 22461023Ethyl 4-[[4-dimethylamino-2-pyrimidinyl]methylamino]-1-piperidinecarboxylateAusbeute 60,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6212ChloroformLösungsmittel

Reaktionsbedingungen

Temperatur
120 °C

Versuchsvorschrift

A mixture of ethyl 4-(methylamino)-1-piperidinecarboxylate (111.75 g) and 2-chloro-N,N-dimethyl-4-pyrimidinamine (47.3 g) is stirred and heated in an oil-bath for 22 hours at 120° C. The reaction mixture is cooled and the product is taken up in trichloromethane (500 ml). Water (300 ml) is added and the layers are separated. The organic phase is washed with water (200 ml), dried, filtered and evaporated. The residue solidifies on triturating in petroleumether. The product is filtered off and crystallized from diisopropyl ether (390 ml). After cooling to 0° C., the product is filtered off and dried, yielding 55.5 g (59.7%) of ethyl 4-[[4-dimethylamino-2-pyrimidinyl]methylamino]-1-piperidinecarboxylate (intermediate 1).

Aufarbeitung

  1. temperatureThe reaction mixture is cooled
  2. customthe layers are separated
  3. washThe organic phase is washed with water (200 ml)
  4. customdried
  5. filtrationfiltered
  6. customevaporated
  7. customon triturating in petroleumether
  8. filtrationThe product is filtered off
  9. customcrystallized from diisopropyl ether (390 ml)
  10. temperatureAfter cooling to 0° C.
  11. filtrationthe product is filtered off
  12. customdried

Quellen und Nachweise

ORD-Eintrag
ord-3203bd07586e4b56911f5f6f004a41ea
Quelldatensatz
uspto-grants-2000_12
Patentnummer
US06159982

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