Water → HCID 68535175, compound

HRID 1993644Notes

Reaction equation

HRID 1993644 reaction equation
Cl[C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][N:3]=1.[C:9]([N:16]1[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]1)([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10].CC(C)([O-])C.[Na+].O>C1(C)C=CC=CC=1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[C:12]([O:11][C:9]([N:16]1[CH2:21][CH2:20][N:19]([C:2]2[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][N:3]=2)[CH2:18][CH2:17]1)=[O:10])([CH3:15])([CH3:13])[CH3:14]

Participants

7

Reactant 4

HCID 962WaterHCID 335152,4-DichloropyridineHCID 143452tert-Butyl piperazine-1-carboxylateHCID 23676156Sodium t-butoxide

Product 1

HCID 68535175HCID 68535175, compound

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 1140TolueneSolvent

Procedure

Stir a solution of 2,4-dichloro-pyridine (6.7 mmol, 1 g), N-Boc piperazine (8.1 mmol, 1.5 g), sodium tert butoxide (9.5 mmol, 0.9 g), palladium (II) acetate (0.7 mmol, 0.15 g) and 2-(di-tbutylphosphino)biphenyl (0.7 mmol, 0.2 g) dissolved in toluene under nitrogen at 100° C. for 4 hours. Cool down to room temperature and add water. Extract in ethyl acetate washing the organic layer with water and saturated aq. sodium chloride. Dry organic layer over sodium sulfate, filter, and concentrate under reduced pressure to give 4-(4-chloro-pyridin-2-yl)-piperazine-1-carboxylic acid tert-butyl ester as a residue. Subject residue to silica gel chromatography eluting with hexanes/ethyl acetate in gradient (from 10% to 50%). MS(ES): m/z=298 [M+H].

Workup

  1. extractionExtract in ethyl acetate washing the organic layer with water and saturated aq. sodium chloride
  2. filtrationDry organic layer over sodium sulfate, filter
  3. concentrationconcentrate under reduced pressure

Sources & evidence

ORD record
ord-fd598760981c4fe9b473389ab45c7402
Source dataset
uspto-grants-2010_01
Patent number
US07652015B2

Reaction notes

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