Water → HCID 17852007, compound

HRID 2403603Notes

Reaction equation

HRID 2403603 reaction equation
[N:1]1([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.Cl[C:15]1[CH:20]=[CH:19][N:18]=[C:17]([CH3:21])[CH:16]=1.C(N(CCCC)CCCC)CCC.O>CN1C(=O)CCC1>[CH3:21][C:17]1[CH:16]=[C:15]([N:4]2[CH2:5][CH2:6][N:1]([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[CH2:2][CH2:3]2)[CH:20]=[CH:19][N:18]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7622TributylamineHCID 143452tert-Butyl piperazine-1-carboxylateHCID 5813924-Chloro-2-methylpyridine

Product 1

HCID 17852007HCID 17852007, compoundYield 89.6%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
150 °C

Procedure

tert-Butyl piperazine-1-carboxylate (500 mg) was dissolved in NMP (10 ml), and 4-chloro-2-methylpyridine (685 mg) and tri-n-butylamine (498 mg) were added thereto, followed by stirring at 150° C. overnight. To the reaction mixture was added water, followed by extraction with EtOAc. The organic layer was dried over MgSO4, and then the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography to obtain tert-butyl 4-(2-methylpyridin-4-yl)piperazine-1-carboxylate (667 mg).

Workup

  1. extractionfollowed by extraction with EtOAc
  2. dry with materialThe organic layer was dried over MgSO4
  3. customthe solvent was evaporated under reduced pressure
  4. customThe obtained residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-b69b5136316b46989b4c058d4834681e
Source dataset
uspto-grants-2014_08
Patent number
US08802679B2

Reaction notes

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