Triethylamine → HCID 67226420, Verbindung

HRID 2367885

Reaktionsgleichung

Reaktionsgleichung von HRID 2367885
[CH3:1][N:2]([CH3:13])[N:3]1[CH2:8][CH2:7][C:6]([NH:11][CH3:12])([C:9]#[N:10])[CH2:5][CH2:4]1.C(N(CC)CC)C.[CH3:21][C:22]1[CH:27]=[C:26]([CH3:28])[CH:25]=[C:24]([CH3:29])[C:23]=1[CH2:30][C:31](Cl)=[O:32].C(=O)(O)[O-].[Na+]>CN(C1C=CN=CC=1)C.O1CCCC1>[C:9]([C:6]1([N:11]([CH3:12])[C:31](=[O:32])[CH2:30][C:23]2[C:22]([CH3:21])=[CH:27][C:26]([CH3:28])=[CH:25][C:24]=2[CH3:29])[CH2:7][CH2:8][N:3]([N:2]([CH3:1])[CH3:13])[CH2:4][CH2:5]1)#[N:10]

Komponenten

7

Edukt 4

HCID 8471TriethylamineHCID 516892Sodium BicarbonateHCID 110307542,4,6-Trimethylbenzeneacetyl chlorideHCID 672253971-Dimethylamino-4-methylamino-piperidine-4-carbonitrile

Produkt 1

HCID 67226420HCID 67226420, VerbindungAusbeute 57,7 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

1.2 g 1-Dimethylamino-4-methylamino-piperidine-4-carbonitrile (from Step 1), 1.67 g triethylamine and 10 mg N,N-Dimethyl-4-aminopyridine are dissolved in 35 ml tetrahydrofuran. The mixture is cooled in an ice bath and a solution of 1.3 g (2,4,6-trimethylphenyl)-acetyl chloride in 20 ml tetrahydrofuran is added. The temperature is kept around 0° C. during addition. Then the mixture is allowed to warm to room temperature and stirred for 18 hours. Then saturated aqueous sodium bicarbonate is added, the mixture is extracted with t-butyl methyl ether, dried over sodium sulfate, and the solvent evaporated. The residue is purified by chromatography on silica gel, using ethyl acetate/acetone (3:1) as a solvent. 1.3 g N-(4-Cyano-1-dimethylamino-piperidin-4-yl)-N-methyl-2-(2,4,6-trimethylphenyl)-acetamide is obtained. 1H-NMR (CDCl3): 6.85 ppm (s, 2H), 3.65 ppm (s, 2H), 3.10 ppm (s, 3H), 3.00 ppm (m, 2H), 2.78 ppm (m, 2H), 2.50 ppm (m, 2H), 2.38 ppm (s, 6H), 2.23 ppm (s, 3H), 2.18 ppm (s, 6H), 1.96 ppm (m, 2H).

Aufarbeitung

  1. temperatureThe mixture is cooled in an ice bath
  2. additionThe temperature is kept around 0° C. during addition
  3. extractionthe mixture is extracted with t-butyl methyl ether
  4. dry with materialdried over sodium sulfate
  5. customthe solvent evaporated
  6. customThe residue is purified by chromatography on silica gel

Quellen und Nachweise

ORD-Eintrag
ord-cdfe178822ee444581a1269bc912365a
Quelldatensatz
uspto-grants-2014_04
Patentnummer
US08703165B2

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