Trifluoroacetic acid → 1-[2-(4-Aminopiperidin-1-yl)ethyl]-7-methoxyquinoxalin-2(1H)-one

HRID 2193111

Reaction equation

HRID 2193111 reaction equation
C(OC(=O)[NH:7][CH:8]1[CH2:13][CH2:12][N:11]([CH2:14][CH2:15][N:16]2[C:25]3[C:20](=[CH:21][CH:22]=[C:23]([O:26][CH3:27])[CH:24]=3)[N:19]=[CH:18][C:17]2=[O:28])[CH2:10][CH2:9]1)(C)(C)C.FC(F)(F)C(O)=O>C(Cl)(Cl)Cl>[NH2:7][CH:8]1[CH2:9][CH2:10][N:11]([CH2:14][CH2:15][N:16]2[C:25]3[C:20](=[CH:21][CH:22]=[C:23]([O:26][CH3:27])[CH:24]=3)[N:19]=[CH:18][C:17]2=[O:28])[CH2:12][CH2:13]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 59398192Tert-butyl(1-(2-(7-methoxy-2-oxoquinoxalin-1(2h)-yl)ethyl)piperidin-4-yl)carbamate

Product 1

HCID 593978381-[2-(4-Aminopiperidin-1-yl)ethyl]-7-methoxyquinoxalin-2(1H)-one

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To 70 mL of a chloroform solution containing 9.53 g of tert-butyl(1-(2-(7-methoxy-2-oxoquinoxalin-1(2H)-yl)ethyl)piperidin-4-yl)carbamate, 20 mL of trifluoroacetic acid was added, and the mixture was stirred at room temperature for 10 hours. The solvent was removed under reduced pressure, the reaction mixture was alkalified with an aqueous saturated sodium hydrogen carbonate solution, and then the solvent was removed under reduced pressure. The residue thus obtained was purified by silica gel column chromatography [silica gel; Chromatorex-NH, manufactured by Fuji Silysia Chemical Ltd., eluent; chloroform:methanol=50:1] to obtain 5.97 g of a brown oily substance, 1-(2-(4-aminopiperidin-1-yl)ethyl)-7-methoxyquinoxalin-2(1H)-one.

Workup

  1. additionwas added
  2. customThe solvent was removed under reduced pressure
  3. customthe solvent was removed under reduced pressure
  4. customThe residue thus obtained
  5. customwas purified by silica gel column chromatography [silica gel; Chromatorex-NH, manufactured by Fuji Silysia Chemical Ltd., eluent; chloroform:methanol=50:1]

Sources & evidence

ORD record
ord-400a81add2684864b0f45c5df6b16131
Source dataset
uspto-grants-2012_12
Patent number
US08329694B2

Linked notes

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