Potassium Carbonate → HCID 58285194, compound

HRID 1257104Notes

Reaction equation

HRID 1257104 reaction equation
[C:1]([N:8]1[CH2:13][CH2:12][N:11]([C:14](=[O:17])[NH:15][CH3:16])[CH2:10][CH2:9]1)(OC(C)(C)C)=O.Cl.CCOC(C)=O.[Cl:25][C:26]1[CH:31]=[C:30](CCl)[CH:29]=[CH:28][N:27]=1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[Cl:25][C:26]1[CH:31]=[C:30]([CH2:1][N:8]2[CH2:9][CH2:10][N:11]([C:14](=[O:17])[NH:15][CH3:16])[CH2:12][CH2:13]2)[CH:29]=[CH:28][N:27]=1

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 111265732-Chloro-4-(chloromethyl)pyridineHCID 20768834tert-Butyl 4-(methylcarbamoyl)piperazine-1-carboxylateHCID 21866389Hydrogen chloride-ethyl acetate

Product 1

HCID 58285194HCID 58285194, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1-Boc-4-(N-methylcarbamoyl)piperazine was treated with 8 M HCl/EtOAc to afford a salt, then the salt (1.0 equiv) was mixed with 2-chloro-4-(chloromethyl)pyridine (1.0 equiv) (Preparation B-11) and K2CO3 (4 equiv) in DMF. The mixture was stirred for 1 h at rt. After removing most of the solvent, the residue was partitioned in water and EtOAc. The organic layer was separated, dried over anhydrous Na2SO4, and evaporated in vacuo. The residue was purified by flash chromatography to give the title compound as a solid (˜90% yield).

Workup

  1. customto afford a salt
  2. customAfter removing most of the solvent
  3. customthe residue was partitioned in water
  4. customThe organic layer was separated
  5. dry with materialdried over anhydrous Na2SO4
  6. customevaporated in vacuo
  7. customThe residue was purified by flash chromatography

Sources & evidence

ORD record
ord-421de3c6519448129cf2e9abaa89b343
Source dataset
uspto-grants-2013_06
Patent number
US08461339B2

Reaction notes

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