tert-Butyl piperazine-1-carboxylate → tert-Butyl 4-(5-methylpyridin-2-yl)piperazine-1-carboxylate

HRID 1957930Notes

Reaction equation

HRID 1957930 reaction equation
C[C:2]1[CH:7]=[CH:6][C:5](Cl)=[CH:4][N:3]=1.[C:9]([O:13][C:14]([N:16]1[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]1)=[O:15])([CH3:12])([CH3:11])[CH3:10].[CH3:22]C(C)([O-])C.[Na+].C1C=CC(P(C2C(C3C(P(C4C=CC=CC=4)C4C=CC=CC=4)=CC=C4C=3C=CC=C4)=C3C(C=CC=C3)=CC=2)C2C=CC=CC=2)=CC=1>C1(C)C=CC=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].C(OCC)C>[C:9]([O:13][C:14]([N:16]1[CH2:21][CH2:20][N:19]([C:2]2[CH:7]=[CH:6][C:5]([CH3:22])=[CH:4][N:3]=2)[CH2:18][CH2:17]1)=[O:15])([CH3:12])([CH3:10])[CH3:11]

Participants

8

Reactant 4

HCID 143452tert-Butyl piperazine-1-carboxylateHCID 634876Binap, (A+-)-HCID 27628695-Chloro-2-methylpyridineHCID 23676156Sodium t-butoxide

Product 1

HCID 45788994tert-Butyl 4-(5-methylpyridin-2-yl)piperazine-1-carboxylate

Reagents, catalysts & solvents 3

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 1140TolueneSolventHCID 3283Diethyl EtherSolvent

Conditions

Temperature
70 °C

Procedure

Under an atmosphere of argon, 2.50 g (19.6 mmol) of 2-methyl-5-chloropyridine and 4.38 g (23.5 mmol) of N-(tert-butyloxycarbonyl)piperazine are dissolved in 50 ml of absolute toluene. 2.26 g (23.5 mmol) of sodium tert-butoxide, 0.37 g (0.59 mmol) of BINAP and 0.36 g (0.39 mmol) of tris(dibenzylideneacetone)dipalladium are then added, and the mixture is heated at 70° C. for 12 h. After cooling, diethyl ether is added to the reaction mixture, the mixture is washed three times with saturated sodium chloride solution and dried over sodium sulphate and the solvent is removed under reduced pressure. The residue is purified by flash chromatography (cyclohexane/ethyl acetate 9:1).

Workup

  1. temperatureAfter cooling
  2. washthe mixture is washed three times with saturated sodium chloride solution
  3. dry with materialdried over sodium sulphate
  4. customthe solvent is removed under reduced pressure
  5. customThe residue is purified by flash chromatography (cyclohexane/ethyl acetate 9:1)

Sources & evidence

ORD record
ord-051c2c558d91453bb59eca4f5883e70a
Source dataset
uspto-grants-2013_04
Patent number
US08410090B2

Reaction notes

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