Hexane → HCID 66977004, compound

HRID 712196Notes

Reaction equation

HRID 712196 reaction equation
Cl.[NH:2]1[CH2:7][CH2:6][CH2:5][CH2:4][CH:3]1[C:8]([O:10][CH2:11][CH3:12])=[O:9].C(=O)([O-])[O-].[K+].[K+].[Br:19][C:20]1[CH:21]=[N:22][C:23](Cl)=[N:24][CH:25]=1.CCCCCC>CN(C=O)C>[Br:19][C:20]1[CH:21]=[N:22][C:23]([N:2]2[CH2:7][CH2:6][CH2:5][CH2:4][CH:3]2[C:8]([O:10][CH2:11][CH3:12])=[O:9])=[N:24][CH:25]=1

Participants

6

Reactant 4

HCID 8058HexaneHCID 11430Potassium CarbonateHCID 6066655-Bromo-2-chloropyrimidineHCID 12436225Ethyl piperidine-2-carboxylate--hydrogen chloride (1/1)

Product 1

HCID 66977004HCID 66977004, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of ethyl piperidine-2-carboxylate hydrochloride (0.5 g, 2.58 mmol) in DMF (15 mL) was added potassium carbonate (1.77 g, 12.89 mmol) at rt. The mixture was stirred at rt for 10 min followed by addition of 5-bromo-2-chloropyrimidine (0.5 g, 2.58 mmol). The reaction was heated up to 80° C. for 3 h. After reaction completion (by TLC), the mixture was poured onto 100 mL ice-cold water and extracted with EtOAc (3×100 mL). The combined organic layer was washed with brine, dried over anhydrous Na2SO4 and evaporated under reduced pressure. The crude residue was purified over 100-200 M silica-gel by using 1.50% EtOAc: hexane to obtain the desired product as an off white solid (0.37 g, 46% yield). MS: 314.08 [M+H]+.

Workup

  1. temperatureThe reaction was heated up to 80° C. for 3 h
  2. customAfter reaction completion (by TLC)
  3. extractionextracted with EtOAc (3×100 mL)
  4. washThe combined organic layer was washed with brine
  5. dry with materialdried over anhydrous Na2SO4
  6. customevaporated under reduced pressure
  7. customThe crude residue was purified over 100-200 M silica-gel

Sources & evidence

ORD record
ord-c89b8155f17d4fe8ba0794a92db4e3d3
Source dataset
uspto-grants-2015_11
Patent number
US09181234B2

Reaction notes

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