Triethylamine → 2-(4-chloro-2,6-dimethyl-phenyl)-N-(4-cyano-1-methoxy-piperidin-4-yl)-N-ethoxy-acetamide

HRID 1473790Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1473790
[CH2:1]([O:3][NH:4][C:5]1([C:13]#[N:14])[CH2:10][CH2:9][N:8]([O:11][CH3:12])[CH2:7][CH2:6]1)[CH3:2].C(N(CC)CC)C.[Cl:22][C:23]1[CH:28]=[C:27]([CH3:29])[C:26]([CH2:30][C:31](Cl)=[O:32])=[C:25]([CH3:34])[CH:24]=1>CN(C)C1C=CN=CC=1.O1CCCC1>[Cl:22][C:23]1[CH:24]=[C:25]([CH3:34])[C:26]([CH2:30][C:31]([N:4]([C:5]2([C:13]#[N:14])[CH2:10][CH2:9][N:8]([O:11][CH3:12])[CH2:7][CH2:6]2)[O:3][CH2:1][CH3:2])=[O:32])=[C:27]([CH3:29])[CH:28]=1

Komponenten

6

Edukt 3

HCID 8471TriethylamineHCID 11746058(4-Chloro-2,6-dimethyl-phenyl)-acetyl chlorideHCID 866574664-Ethoxyamino-1-methoxy-piperidine-4-carbonitrile

Produkt 1

HCID 584280062-(4-chloro-2,6-dimethyl-phenyl)-N-(4-cyano-1-methoxy-piperidin-4-yl)-N-ethoxy-acetamide

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 8028TetrahydrofuranLösungsmittel2×

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a solution of 4-ethoxyamino-1-methoxy-piperidine-4-carbonitrile (2.0 g, 10.04 mmol), triethylamine (3.49 ml, 2.54 g, 25.09 mmol) and a catalytic amount of 4-dimethylamino-pyridine in tetrahydrofuran (10 ml) at 0° C. was added a solution of (4-chloro-2,6-dimethyl-phenyl)-acetyl chloride (2.18 g, 10.04 mmol) in tetrahydrofuran (1 ml) dropwise. The suspension was stirred at 0° C. for 15 minutes, and at room temperature overnight. The reaction mixture was evaporated, diluted with ethyl acetate and water, and the layers separated. The aqueous phase was extracted with ethyl acetate, the combined organic layers washed with brine, dried over sodium sulfate and concentrated. The crude material was triturated with diisopropyl ether, filtered and the filtrate concentrated. The oily residue was purified by chromatography on silica gel (ethyl acetate/hexane 1:1). Yield: 1.53 g of 2-(4-chloro-2,6-dimethyl-phenyl)-N-(4-cyano-1-methoxy-piperidin-4-yl)-N-ethoxy-acetamide (title compound P3ii.49) as a colorless oil, which solidified upon standing, mp 100-103° C.

Aufarbeitung

  1. customat room temperature
  2. customovernight
  3. customThe reaction mixture was evaporated
  4. additiondiluted with ethyl acetate and water
  5. customthe layers separated
  6. extractionThe aqueous phase was extracted with ethyl acetate
  7. washthe combined organic layers washed with brine
  8. dry with materialdried over sodium sulfate
  9. concentrationconcentrated
  10. customThe crude material was triturated with diisopropyl ether
  11. filtrationfiltered
  12. concentrationthe filtrate concentrated
  13. customThe oily residue was purified by chromatography on silica gel (ethyl acetate/hexane 1:1)

Quellen und Nachweise

ORD-Eintrag
ord-1311e4a590214952bc7d68410613465d
Quelldatensatz
uspto-grants-2015_04
Patentnummer
US09018135B2

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