Triethylamine → 1-(2,6-Dimethylpyrimidin-4-yl)-4-(ethoxycarbonyl)piperidine

HRID 2289540Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2289540
[CH3:1][C:2]1[N:7]=[C:6](Cl)[CH:5]=[C:4]([CH3:9])[N:3]=1.[NH:10]1[CH2:20][CH2:19][CH:13]([C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH2:12][CH2:11]1.C(N(CC)CC)C>C(O)C>[CH3:1][C:2]1[N:7]=[C:6]([N:10]2[CH2:20][CH2:19][CH:13]([C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH2:12][CH2:11]2)[CH:5]=[C:4]([CH3:9])[N:3]=1

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 70770Ethyl 4-piperidinecarboxylateHCID 31541994-Chloro-2,6-dimethylpyrimidine

Produkt 1

HCID 186980321-(2,6-Dimethylpyrimidin-4-yl)-4-(ethoxycarbonyl)piperidineAusbeute 92,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel2×

Versuchsvorschrift

2,6-Dimethyl-4-chloro-pyrimidine (1.0 g) in ethanol (10 ml) was added slowly to a solution of ethyl isonipecotate (1.1 g) and triethylamine (2.0 ml) in ethanol (20 ml). The reaction was stirred at room temperature overnight. The solvent was removed in vacuo and the residue was partitioned between ethyl acetate and water, washed with water (2×50 ml), dried and evaporated to give 1-(2,6-dimethylpyrimidin-4-yl)-4-(ethoxycarbonyl)piperidine as an oil (1.71 g); NMR (CDCl3): 1.25 (t, 3H), 1.65-1.80 (m, 4H), 1.95-2.00 (m, 2H), 2.55 (s, 3H), 2.45 (s, 3H), 2.50-2.60 (m, 1H), 3.00 (dt, 2H), 4.15 (q, 2H), 4.35 (d, 2H), 6.2 (s, 1H).

Aufarbeitung

  1. customThe solvent was removed in vacuo
  2. customthe residue was partitioned between ethyl acetate and water
  3. washwashed with water (2×50 ml)
  4. customdried
  5. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-8511c32afedf4a8d9e3cabf7e171d583
Quelldatensatz
uspto-grants-2000_07
Patentnummer
US06093718

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