Hydrochloric Acid → Methyl 2-[1-(2-methyl-4-quinolyl)piperazin-2-yl]acetate

HRID 333982Notes

Reaction equation

HRID 333982 reaction equation
[CH3:1][O:2][C:3](=[O:29])[CH2:4][CH:5]1[N:10]([C:11]2[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[N:14]=[C:13]([CH3:21])[CH:12]=2)[CH2:9][CH2:8][N:7](C(OC(C)(C)C)=O)[CH2:6]1.Cl>O1CCOCC1.C(OCC)C>[CH3:21][C:13]1[CH:12]=[C:11]([N:10]2[CH2:9][CH2:8][NH:7][CH2:6][CH:5]2[CH2:4][C:3]([O:2][CH3:1])=[O:29])[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[N:14]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 86691601tert-Butyl 3-(2-methoxy-2-oxo-ethyl)-4-(2-methyl-4-quinolyl)piperazine-1-carboxylate

Product 1

HCID 66835808Methyl 2-[1-(2-methyl-4-quinolyl)piperazin-2-yl]acetateYield 90.4%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 312751,4-DioxaneSolvent2×

Procedure

tert-Butyl 3-(2-methoxy-2-oxo-ethyl)-4-(2-methyl-4-quinolyl)piperazine-1-carboxylate (239 mg, 0.28 mmol) was dissolved in dioxane (1 ml), combined with a solution of HCl in dioxane (4N, 4 ml, 16 mmol) and stirred overnight. The mixture was diluted with diethylether, the precipitate was collected by filtration and dissolved in DCM. The solution was washed with a saturated solution of sodium bicarbonate and dried over sodium sulfate. The solvent was removed under reduced pressure, the residue was triturated with diethylether to yield 85 mg of a yellow solid (0.253 mmol, 72%).

Workup

  1. filtrationthe precipitate was collected by filtration
  2. dissolutiondissolved in DCM
  3. washThe solution was washed with a saturated solution of sodium bicarbonate
  4. dry with materialdried over sodium sulfate
  5. customThe solvent was removed under reduced pressure
  6. customthe residue was triturated with diethylether

Sources & evidence

ORD record
ord-d0fc0e4ec99b411aa6083db574595b84
Source dataset
uspto-grants-2014_11
Patent number
US08883791B2

Reaction notes

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