tert-Butyl piperazine-1-carboxylate → HCID 70873435, compound

HRID 2172203Notes

Reaction equation

HRID 2172203 reaction equation
Cl[C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([O:12]C3CCCCO3)[CH:8]=2)[N:3]=1.[C:19]([O:23][C:24]([N:26]1[CH2:31][CH2:30][NH:29][CH2:28][CH2:27]1)=[O:25])([CH3:22])([CH3:21])[CH3:20].C(=O)([O-])O.[Na+]>>[C:19]([O:23][C:24]([N:26]1[CH2:31][CH2:30][N:29]([C:2]2[CH:11]=[CH:10][C:9]3[C:4](=[CH:5][CH:6]=[C:7]([OH:12])[CH:8]=3)[N:3]=2)[CH2:28][CH2:27]1)=[O:25])([CH3:22])([CH3:20])[CH3:21]

Participants

4

Reactant 3

HCID 143452tert-Butyl piperazine-1-carboxylateHCID 516892Sodium BicarbonateHCID 86709380HCID 86709380, compound

Product 1

HCID 70873435HCID 70873435, compound

Procedure

2-Chloro-6-(tetrahydropyran-2-yloxy)quinoline (1.00 g) and piperazine-1-carboxylic acid tert-butyl ester (0.76 g) were heated to 140° C. in the absence of solvent under an argon atmosphere and stirred for 2 hours. After cooling the reaction mixture to room temperature, a sodium hydrogen carbonate aqueous solution was added thereto, followed by extraction with dichloromethane. The organic layer was washed with a saturated sodium chloride aqueous solution and dried over magnesium sulfate. The result was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (hexane:ethyl acetate=75:25→67:33). The result was concentrated to dryness under reduced pressure to afford the title compound as a pale yellow amorphous compound (0.55 g).

Workup

  1. extractionfollowed by extraction with dichloromethane
  2. washThe organic layer was washed with a saturated sodium chloride aqueous solution
  3. dry with materialdried over magnesium sulfate
  4. concentrationThe result was concentrated under reduced pressure
  5. customthe residue was purified by silica gel column chromatography (hexane:ethyl acetate=75:25→67:33)
  6. concentrationThe result was concentrated to dryness under reduced pressure

Sources & evidence

ORD record
ord-879158e30760435d8ea41b4f593e0f74
Source dataset
uspto-grants-2015_06
Patent number
US09051333B2

Reaction notes

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