Acetic Acid → 2-(4-Isopropylpiperazin-1-yl)isonicotinonitrile

HRID 276780ノート

反応式

HRID 276780 の反応式
[N:1]1([C:7]2[CH:8]=[C:9]([CH:12]=[CH:13][N:14]=2)[C:10]#[N:11])[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.C(O)(=O)C.[CH3:19][C:20]([CH3:22])=O.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[OH-].[Na+]>ClCCl>[CH:20]([N:4]1[CH2:3][CH2:2][N:1]([C:7]2[CH:8]=[C:9]([CH:12]=[CH:13][N:14]=2)[C:10]#[N:11])[CH2:6][CH2:5]1)([CH3:22])[CH3:19]

参加物

7

反応物 5

HCID 176Acetic AcidHCID 180AcetoneHCID 14798Sodium HydroxideHCID 5049666Sodium triacetoxyborohydrideHCID 162279862-(Piperazin-1-yl)pyridine-4-carbonitrile

生成物 1

HCID 186715252-(4-Isopropylpiperazin-1-yl)isonicotinonitrile収率 59%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

To a solution of 2-piperazin-1-yl-isonicotinonitrile (10 g, 53 mmol), glacial acetic acid (4.26 ml, 4.5 g, 74.4 mmol, 1.4 equiv) and acetone (4.29 ml, 3.39 g, 58 mmol, 1.1 equiv) in anhydrous dichloromethane was added sodium triacetoxyborohydride (13.5 g, 63.8 mmol, 1.2 equiv). The reaction was stirred overnight, then an aqueous solution of 1 N NaOH solution was added (150 ml) and the mixture was extracted once with dichloromethane, then twice with a solution of 10% methanol/dichloromethane. The organic layers were combined, dried over anhydrous sodium sulfate, filtered, and concentrated in vacuo. Purification of the residue by flash column chromatography (5% methanol/CH2Cl2 grading to 10% methanol/CH2Cl2) provided the desired product (6.52 g, 59%).

後処理

  1. extractionthe mixture was extracted once with dichloromethane
  2. dry with materialdried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customPurification of the residue by flash column chromatography (5% methanol/CH2Cl2 grading to 10% methanol/CH2Cl2)

出典と根拠

ORDレコード
ord-e14bb971f8be4335955395148d3cd03f
出典データセット
uspto-grants-2002_03
特許番号
US06355635B1

反応ノート

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