Ammonia → 2-(5'-Bromo-3,4,5,6-tetrahydro-2H-[1,2]bipyridinyl-4-yl)ethylamine

HRID 1403695Notes

Reaction equation

HRID 1403695 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[CH2:13][CH2:12][CH:11]([CH2:14][CH2:15][NH:16]C(=O)OC(C)(C)C)[CH2:10][CH2:9]2)=[N:6][CH:7]=1.FC(F)(F)C(O)=O.N>ClCCl>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[CH2:9][CH2:10][CH:11]([CH2:14][CH2:15][NH2:16])[CH2:12][CH2:13]2)=[N:6][CH:7]=1

Participants

5

Reactant 3

HCID 222AmmoniaHCID 6422Trifluoroacetic acidHCID 66661183tert-butyl 2-(5'-bromo-3,4,5,6-tetrahydro-2H-[1,2]bipyridinyl-4-yl)ethylcarbamate

Product 1

HCID 625867352-(5'-Bromo-3,4,5,6-tetrahydro-2H-[1,2]bipyridinyl-4-yl)ethylamine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 6.9 g (17.95 mmol) of tert-butyl 2-(5′-bromo-3,4,5,6-tetrahydro-2H-[1,2]bipyridinyl-4-yl)ethylcarbamate obtained in step 8.1., in 100 ml of dichloromethane, cooled by an ice/water bath, is admixed slowly with 20.47 g (179.54 mmol) of trifluoroacetic acid. Stirring is continued at ambient temperature for 2 hours. The reaction mixture is poured into a mixture of ice-water and 28% aqueous ammonia. The mixture is decanted, the aqueous phase is extracted twice with dichloromethane, and the combined organic phases are washed with saturated aqueous sodium chloride solution, dried over sodium sulphate and concentrated under reduced pressure.

Workup

  1. customThe mixture is decanted
  2. extractionthe aqueous phase is extracted twice with dichloromethane
  3. washthe combined organic phases are washed with saturated aqueous sodium chloride solution
  4. dry with materialdried over sodium sulphate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-9d105bb640be4a039ce554499606e5ea
Source dataset
uspto-grants-2014_12
Patent number
US08912218B2

Reaction notes

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