Piperazine → 5-Chloro-4,6-dimethyl-2-(piperazin-1-yl)pyridine-3-carbonitrile

HRID 1775357ノート

反応式

HRID 1775357 の反応式
Cl[C:2]1[N:9]=[C:8]([CH3:10])[C:7]([Cl:11])=[C:6]([CH3:12])[C:3]=1[C:4]#[N:5].C([O-])([O-])=O.[K+].[K+].[NH:19]1[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]1>>[Cl:11][C:7]1[C:6]([CH3:12])=[C:3]([C:4]#[N:5])[C:2]([N:19]2[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]2)=[N:9][C:8]=1[CH3:10]

参加物

4

反応物 3

HCID 4837PiperazineHCID 11430Potassium CarbonateHCID 3348522,5-Dichloro-4,6-dimethylpyridine-3-carbonitrile

生成物 1

HCID 898255905-Chloro-4,6-dimethyl-2-(piperazin-1-yl)pyridine-3-carbonitrile収率 93%

反応条件

温度
120 °C

実験手順

A mixture of 2,5-dichloro-4,6-dimethylnicotinonitrile (200 mg, 0.995 mmol), K2CO3 (275 mg, 1.990 mmol) and piperazine (5141 mg, 59.7 mmol) was heated under microwave heating at 120° C. for 15 minutes. After cooling to room temperature the mixture was partitioned between 1N HCl and DCM. The layers were separated and the aqueous layer was extracted once with DCM, basified with NaOH (4N) and extracted with DCM (4×). The combined organic layers were dried (sodium sulfate) and concentrated under reduced pressure to give 231 mg of a solid (0.922 mmol, yield 93%) MS (multi-mode) m/z=251.2 [M+1]+.

後処理

  1. temperaturewas heated under microwave
  2. temperatureAfter cooling to room temperature the mixture
  3. customwas partitioned between 1N HCl and DCM
  4. customThe layers were separated
  5. extractionthe aqueous layer was extracted once with DCM
  6. extractionextracted with DCM (4×)
  7. dry with materialThe combined organic layers were dried (sodium sulfate)
  8. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-34fe9bdd99214a1f8ea6dd5d98de2860
出典データセット
uspto-grants-2016_02
特許番号
US09260441B2

反応ノート

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