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

HRID 19784

Reaction equation

HRID 19784 reaction equation
[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]

Participants

7

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 14798Sodium HydroxideSolvent

Conditions

Temperature
105 °C

Procedure

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)+.

Workup

  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

Sources & evidence

ORD record
ord-ebe208f56ec54742a4158767aa63b045
Source dataset
uspto-grants-2010_06
Patent number
US07745477B2

Linked notes

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