Triethylamine → N-(4-Cyano-1-dimethylamino-piperidin-4-yl)-2-(2,4,6-trimethyl-phenyl)-acetamide

HRID 2367881노트

반응식

HRID 2367881 반응식
[NH2:1][C:2]1([C:11]#[N:12])[CH2:7][CH2:6][N:5]([N:8]([CH3:10])[CH3:9])[CH2:4][CH2:3]1.C(N(CC)CC)C.[CH3:20][C:21]1[CH:26]=[C:25]([CH3:27])[CH:24]=[C:23]([CH3:28])[C:22]=1[CH2:29][C:30](Cl)=[O:31].C(=O)(O)[O-].[Na+]>CN(C1C=CN=CC=1)C.O1CCCC1>[C:11]([C:2]1([NH:1][C:30](=[O:31])[CH2:29][C:22]2[C:21]([CH3:20])=[CH:26][C:25]([CH3:27])=[CH:24][C:23]=2[CH3:28])[CH2:3][CH2:4][N:5]([N:8]([CH3:9])[CH3:10])[CH2:6][CH2:7]1)#[N:12]

참가 물질

7

반응물 4

HCID 8471TriethylamineHCID 516892Sodium BicarbonateHCID 110307542,4,6-Trimethylbenzeneacetyl chlorideHCID 672253764-Amino-1-dimethylamino-piperidine-4-carbonitrile

생성물 1

HCID 67226228N-(4-Cyano-1-dimethylamino-piperidin-4-yl)-2-(2,4,6-trimethyl-phenyl)-acetamide수율 80.6%

시약·촉매·용매 2

HCID 142844-(Dimethylamino)pyridine촉매HCID 8028Tetrahydrofuran용매2회

실험 절차

920 mg 4-Amino-1-dimethylamino-piperidine-4-carbonitrile (from Step 1), 1.38 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 1.07 g (2,4,6-trimethyl-phenyl)-acetyl chloride in 15 ml tetrahydrofuran is added. The temperature is kept around 3° C. during addition. Then the mixture is allowed to warm to room temperature and stirred for 2 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. Thus, 1.44 g N-(4-Cyano-1-dimethylamino-piperidin-4-yl)-2-(2,4,6-trimethyl-phenyl)-acetamide is obtained as an off-white solid. 1H-NMR (CDCl3): 6.90 ppm (s, 2H), 5.20 ppm (s, 1H), 3.60 ppm (s, 2H), 2.70 ppm (m, 4H), 2.36 ppm (m, 2H), 2.33 ppm (s, 6H), 2.28 ppm (s, 3H), 2.23 ppm (s, 6H), 1.72 ppm (m, 2H).

후처리

  1. temperatureThe mixture is cooled in an ice bath
  2. additionThe temperature is kept around 3° C. during addition
  3. extractionthe mixture is extracted with t-butyl methyl ether
  4. dry with materialdried over sodium sulfate
  5. customthe solvent evaporated

출처 및 근거

ORD 기록
ord-d1476196564b4faf8be5dee62ecd554e
출처 데이터셋
uspto-grants-2014_04
특허 번호
US08703165B2

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