tert-butyl (1-(2-(2-oxo-1,8-naphthyridin-1(2H)-yl)ethyl)piperidin-4-yl)carbamate → 1-(2-(4-aminopiperidin-1-yl)ethyl)-1,8-naphthyridin-2(1H)-one

HRID 385505Notes

Reaction equation

HRID 385505 reaction equation
[O:1]=[C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[N:5][CH:6]=[CH:7][CH:8]=2)[N:3]1[CH2:12][CH2:13][N:14]1[CH2:19][CH2:18][CH:17]([NH:20]C(=O)OC(C)(C)C)[CH2:16][CH2:15]1>ClCCl.FC(F)(F)C(O)=O>[NH2:20][CH:17]1[CH2:18][CH2:19][N:14]([CH2:13][CH2:12][N:3]2[C:4]3[C:9](=[CH:8][CH:7]=[CH:6][N:5]=3)[CH:10]=[CH:11][C:2]2=[O:1])[CH2:15][CH2:16]1

Participants

4

Reactant 1

HCID 57815416tert-butyl (1-(2-(2-oxo-1,8-naphthyridin-1(2H)-yl)ethyl)piperidin-4-yl)carbamate

Product 1

HCID 578152591-(2-(4-aminopiperidin-1-yl)ethyl)-1,8-naphthyridin-2(1H)-oneYield 78.9%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

To a solution of 0.26 g of tert-butyl (1-(2-(2-oxo-1,8-naphthyridin-1(2H)-yl)ethyl)piperidin-4-yl)carbamate in 4 mL of dichloromethane, 2 mL of trifluoroacetic acid was added, and the mixture was stirred at room temperature for 2 hours. The solvent was distilled off under reduced pressure, water and diethyl ether was added to the resultant residue, and the aqueous layer was separated and washed with diethyl ether, and then, thereto was added a 20% aqueous sodium hydroxide solution and the reaction mixture was adjusted to pH 13 to 14. Thereto were added dichloromethane and sodium chloride, the organic layer was separated, and the aqueous layer was extracted with chloroform while being salted out. The organic layer and the extract were combined, the resultant solution was dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure to obtain 0.15 g of 1-(2-(4-aminopiperidin-1-yl)ethyl)-1,8-naphthyridin-2(1H)-one as a yellow oily substance.

Workup

  1. distillationThe solvent was distilled off under reduced pressure, water and diethyl ether
  2. additionwas added to the resultant residue
  3. customthe aqueous layer was separated
  4. washwashed with diethyl ether
  5. additionwas added a 20% aqueous sodium hydroxide solution
  6. additionThereto were added dichloromethane and sodium chloride
  7. customthe organic layer was separated
  8. extractionthe aqueous layer was extracted with chloroform
  9. dry with materialthe resultant solution was dried over anhydrous magnesium sulfate
  10. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-6cd2bafda9724038ae4e3e0afc540bde
Source dataset
uspto-grants-2013_02
Patent number
US08367831B2

Reaction notes

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