Ethanol hydrochloride → 1-[2-(4-amino-1-piperidinyl)ethyl]-7-fluoro-1,5-naphthyridin-2(1H)-one

HRID 385611Notes

Reaction equation

HRID 385611 reaction equation
[F:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][C:8](=[O:28])[N:9]2[CH2:12][CH2:13][N:14]2[CH2:19][CH2:18][CH:17]([NH:20]C(=O)OC(C)(C)C)[CH2:16][CH2:15]2)=[N:4][CH:3]=1.Cl.C(O)C>C(Cl)(Cl)Cl>[NH2:20][CH:17]1[CH2:16][CH2:15][N:14]([CH2:13][CH2:12][N:9]2[C:10]3[C:5](=[N:4][CH:3]=[C:2]([F:1])[CH:11]=3)[CH:6]=[CH:7][C:8]2=[O:28])[CH2:19][CH2:18]1

Participants

4

Reactant 2

HCID 21887872Ethanol hydrochlorideHCID 57815181tert-butyl (1-(2-(7-fluoro-2-oxo-1,5-naphthyridin-1(2H)-yl)ethyl)piperidin-4-yl)carbamate

Product 1

HCID 578151991-[2-(4-amino-1-piperidinyl)ethyl]-7-fluoro-1,5-naphthyridin-2(1H)-oneYield 96%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
40 °C

Procedure

A solution of 0.59 g of tert-butyl (1-(2-(7-fluoro-2-oxo-1,5-naphthyridin-1(2H)-yl)ethyl)piperidin-4-yl)carbamate in 30 mL of a 2 mol/L hydrogen chloride/ethanol was stirred at room temperature for 18 hours. To the reaction mixture, 2 mL of chloroform was added, and the mixture was stirred at 40° C. for 4 hours, and stirred at room temperature for 18 hours. In the reaction mixture, the solvent was distilled off under reduced pressure, the mixture was neutralized with a saturated aqueous sodium hydrogen carbonate solution, and then the solvent was distilled off under reduced pressure. The resultant residue was washed with ethanol and, in the mother liquid, the solvent was distilled off under reduced pressure, and the resultant residue was purified with silica gel column chromatography using silica gel; Chromatorex-NH made by Fuji Silysia Chemical Ltd. and an eluent of chloroform:methanol=10:1 to obtain 421 mg of 1-(2-(4-aminopiperidin-1-yl)ethyl)-7-fluoro-1,5-naphthyridin-2(1H)-one as a light yellow solid.

Workup

  1. stirringstirred at room temperature for 18 hours
  2. distillationIn the reaction mixture, the solvent was distilled off under reduced pressure
  3. distillationthe solvent was distilled off under reduced pressure
  4. washThe resultant residue was washed with ethanol and, in the mother liquid
  5. distillationthe solvent was distilled off under reduced pressure
  6. customthe resultant residue was purified with silica gel column chromatography

Sources & evidence

ORD record
ord-ca0d23967f5f4c97ba3ea59b9ae3c63a
Source dataset
uspto-grants-2013_02
Patent number
US08367831B2

Reaction notes

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