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

HRID 2074075Notes

Reaction equation

HRID 2074075 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 argon atmosphere, 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 a saturated sodium chloride solution and dried over sodium sulfate and the solvent is removed in vacuo. The residue is purified by flash chromatography (cyclohexane/ethyl acetate 9:1).

Workup

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

Sources & evidence

ORD record
ord-8ef16fb1b63747939cc2eae8138a3910
Source dataset
uspto-grants-2011_04
Patent number
US07919489B2

Reaction notes

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