(3-Isopropoxy-4-nitrophenyl)(1-methylpiperidin-4-yl)amine → 2-isopropoxy-N4-(1-methylpiperidin-4-yl)benzene-1,4-diamine

HRID 518856ノート

反応式

HRID 518856 の反応式
[CH:1]([O:4][C:5]1[CH:6]=[C:7]([NH:14][CH:15]2[CH2:20][CH2:19][N:18]([CH3:21])[CH2:17][CH2:16]2)[CH:8]=[CH:9][C:10]=1[N+:11]([O-])=O)([CH3:3])[CH3:2]>C(O)C.[Pd]>[CH:1]([O:4][C:5]1[CH:6]=[C:7]([NH:14][CH:15]2[CH2:16][CH2:17][N:18]([CH3:21])[CH2:19][CH2:20]2)[CH:8]=[CH:9][C:10]=1[NH2:11])([CH3:3])[CH3:2]

参加物

4

反応物 1

HCID 83005936(3-Isopropoxy-4-nitrophenyl)(1-methylpiperidin-4-yl)amine

生成物 1

HCID 830025872-isopropoxy-N4-(1-methylpiperidin-4-yl)benzene-1,4-diamine収率 67.3%

試薬・触媒・溶媒 2

HCID 23938Palladium触媒HCID 702Ethanol溶媒

実験手順

A mixture of 1.49 g of (3-isopropoxy-4-nitrophenyl)(1-methylpiperidin-4-yl)amine and 150 mg of 10% palladium-on-carbon in 60 ml of ethanol is hydrogenated at 25° C. under 1 bar for 3 h. The mixture is filtered on Clarcel and the Clarcel is rinsed with ethanol. The filtrate is concentrated to dryness under reduced pressure and the residue is purified by chromatography on a 70 g silica cartridge, elution being carried out with a 96.5/3/0.5 v/v/v dichloromethane/methanol/28% aqueous ammonia mixture at a flow rate of 50 ml/min, so as to obtain 0.9 g of 2-isopropoxy-N4-(1-methylpiperidin-4-yl)benzene-1,4-diamine in the form of a brown liquid.

後処理

  1. filtrationThe mixture is filtered on Clarcel
  2. washthe Clarcel is rinsed with ethanol
  3. concentrationThe filtrate is concentrated to dryness under reduced pressure
  4. customthe residue is purified by chromatography on a 70 g silica cartridge, elution

出典と根拠

ORDレコード
ord-d4afad75af8144bda3a82c3fe9c381f1
出典データセット
uspto-grants-2015_08
特許番号
US09115140B2

反応ノート

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