Acetic Acid → (4-Tert-butyl-benzyl)-[2-(2-chloro-pyridin-4-yl)-ethyl]-amine

HRID 19784

反応式

HRID 19784 の反応式
[Cl:1][C:2]1[CH:7]=[C:6]([C:8]#[CH:9])[CH:5]=[CH:4][N:3]=1.[C:10]([C:14]1[CH:21]=[CH:20][C:17]([CH2:18][NH2:19])=[CH:16][CH:15]=1)([CH3:13])([CH3:12])[CH3:11].C(O)(=O)C.C([BH3-])#N.[Na+]>C(O)C.[OH-].[Na+]>[C:10]([C:14]1[CH:15]=[CH:16][C:17]([CH2:18][NH:19][CH2:9][CH2:8][C:6]2[CH:5]=[CH:4][N:3]=[C:2]([Cl:1])[CH:7]=2)=[CH:20][CH:21]=1)([CH3:13])([CH3:11])[CH3:12]

参加物

7

反応物 4

HCID 176Acetic AcidHCID 27356554-tert-ButylbenzylamineHCID 5003444Sodium cyanoborohydrideHCID 234368312-Chloro-4-ethynylpyridine

生成物 1

HCID 86613990(4-Tert-butyl-benzyl)-[2-(2-chloro-pyridin-4-yl)-ethyl]-amine収率 55.4%

試薬・触媒・溶媒 2

HCID 702Ethanol溶媒HCID 14798Sodium Hydroxide溶媒

反応条件

温度
105 °C

実験手順

A mixture of 1.386 g of 2-chloro-4-ethynyl-pyridine (10.07 mmol), 2.65 ml of 4-tert-butyl-benzylamine (15.11 mmol), 0.58 ml of acetic acid (10.07 mmol) and 666 mg of sodium cyanoborohydride (95% purity, 10.07 mmol) in ethanol (12 ml) were heated to 105° C. in a sealed tube for 2 d. The reaction mixture was allowed to cool to RT, diluted with 3N NaOH solution and extracted with DCM. The combined organic extracts were washed with saturated NaHCO3 solution and brine, dried (Na2SO4), filtered and concentrated in vacuo. After column chromatography (heptane/EtOAc 100:0 to 0:100) 1.688 g (55%) of the title compound were isolated as a brown liquid. MS (ISP) 303.2 (M+H)+.

後処理

  1. temperatureto cool to RT
  2. extractionextracted with DCM
  3. washThe combined organic extracts were washed with saturated NaHCO3 solution and brine
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-ebe208f56ec54742a4158767aa63b045
出典データセット
uspto-grants-2010_06
特許番号
US07745477B2

関連ノート

読み込み中…