Triethylamine → HCID 67226420, 화합물

HRID 2367885

반응식

HRID 2367885 반응식
[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]

참가 물질

7

반응물 4

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

생성물 1

HCID 67226420HCID 67226420, 화합물수율 57.7%

시약·촉매·용매 2

HCID 142844-(Dimethylamino)pyridine촉매HCID 8028Tetrahydrofuran용매2회

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-cdfe178822ee444581a1269bc912365a
출처 데이터셋
uspto-grants-2014_04
특허 번호
US08703165B2

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