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

HRID 19784

반응식

HRID 19784 반응식
[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]

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 702Ethanol용매HCID 14798Sodium Hydroxide용매

반응 조건

온도
105 °C

실험 절차

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)+.

후처리

  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

출처 및 근거

ORD 기록
ord-ebe208f56ec54742a4158767aa63b045
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07745477B2

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