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

HRID 1473790ノート

反応式

HRID 1473790 の反応式
[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

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 142844-(Dimethylamino)pyridine触媒HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
0 °C

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-1311e4a590214952bc7d68410613465d
出典データセット
uspto-grants-2015_04
特許番号
US09018135B2

反応ノート

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