Piperidine → Diethyl 2-amino-4-(4-cyanophenyl)-6-methyl-1-[3-(trifluoromethyl)phenyl]-1,4-dihydro-3,5-pyridinedicarboxylate

HRID 1766350Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1766350
C([CH2:3][CH2:4][O:5][C:6](=[O:8])C)#N.[C:9]([C:11]1[CH:18]=CC(C=O)=[CH:13][CH:12]=1)#[N:10].[NH:19]1[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]1.[CH2:25]([O:27][C:28](=[O:43])[CH:29]=[C:30]([NH:32][C:33]1[CH:38]=[CH:37][CH:36]=[C:35]([C:39]([F:42])([F:41])[F:40])[CH:34]=1)[CH3:31])[CH3:26]>C(O)C>[NH2:19][C:24]1[N:32]([C:33]2[CH:38]=[CH:37][CH:36]=[C:35]([C:39]([F:40])([F:42])[F:41])[CH:34]=2)[C:30]([CH3:31])=[C:29]([C:28]([O:27][CH2:25][CH3:26])=[O:43])[CH:22]([C:21]2[CH:13]=[CH:12][C:11]([C:9]#[N:10])=[CH:18][CH:20]=2)[C:23]=1[C:6]([O:5][CH2:4][CH3:3])=[O:8]

Komponenten

6

Edukt 4

HCID 8082Piperidine2×HCID 660424-CyanobenzaldehydeHCID 2192242-Cyanoethyl acetateHCID 68427624Ethyl-3-{[3-(trifluoromethyl)phenyl]amino}-2-butenoate

Produkt 1

HCID 10345841Diethyl 2-amino-4-(4-cyanophenyl)-6-methyl-1-[3-(trifluoromethyl)phenyl]-1,4-dihydro-3,5-pyridinedicarboxylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel2×

Versuchsvorschrift

Cyanoethylacetate (2.07 g, 18.3 mmol) and 4-cyanobenzaldehyde (2.40 g, 18.3 mmol) are dissolved in ethanol (125 ml) under an argon atmosphere. Piperidine (46.7 mg, 0.55 mmol) is added, and the reaction mixture is stirred for 2 hours at room temperature. An ethanol (300 ml) solution of Example 1A (5.00 g, 18.3 mmol) and additional piperidine (0.156 g, 1.83 mmol) is added, and the reaction mixture is stirred at reflux for 16 hours. The reaction mixture is concentrated in vacuo and chromatographed over silica get with cyclohexane/ethyl acetate mixtures to give a pale yellow oil.

Aufarbeitung

  1. stirringthe reaction mixture is stirred
  2. temperatureat reflux for 16 hours
  3. concentrationThe reaction mixture is concentrated in vacuo
  4. customchromatographed over silica
  5. customget with cyclohexane/ethyl acetate
  6. customto give a pale yellow oil

Quellen und Nachweise

ORD-Eintrag
ord-ef3ca186367143c385c1a8b9bedf758c
Quelldatensatz
uspto-grants-2007_06
Patentnummer
US07230017B2

Notizen zur Reaktion

Wird geladen…