Hydrogen chloride-ethyl acetate → 1-(2-(4-aminopiperidin-1-yl)ethyl)-7-methoxy-1,8-naphthyridin-2(1H)-one hydrochloride

HRID 1510633Notes

Reaction equation

HRID 1510633 reaction equation
[CH3:1][O:2][C:3]1[N:12]=[C:11]2[C:6]([CH:7]=[CH:8][C:9](=[O:29])[N:10]2[CH2:13][CH2:14][N:15]2[CH2:20][CH2:19][CH:18]([NH:21]C(=O)OC(C)(C)C)[CH2:17][CH2:16]2)=[CH:5][CH:4]=1.[ClH:30].C(OCC)(=O)C>>[ClH:30].[NH2:21][CH:18]1[CH2:17][CH2:16][N:15]([CH2:14][CH2:13][N:10]2[C:11]3[C:6](=[CH:5][CH:4]=[C:3]([O:2][CH3:1])[N:12]=3)[CH:7]=[CH:8][C:9]2=[O:29])[CH2:20][CH2:19]1

Participants

3

Reactant 2

HCID 21866389Hydrogen chloride-ethyl acetateHCID 57815232tert-butyl (1-(2-(7-methoxy-2-oxo-1,8-naphthyridin-1(2H)-yl)ethyl)piperidin-4-yl)carbamate

Product 1

HCID 689247211-(2-(4-aminopiperidin-1-yl)ethyl)-7-methoxy-1,8-naphthyridin-2(1H)-one hydrochloride

Procedure

To 2.8 g of tert-butyl (1-(2-(7-methoxy-2-oxo-1,8-naphthyridin-1(2H)-yl)ethyl)piperidin-4-yl)carbamate, 50 mL of a 4 mol/L hydrogen chloride/ethyl acetate solution was added, and the mixture was stirred at room temperature for 29 hours. The solvent was distilled off under reduced pressure, ethyl acetate was added to the solid thus obtained, and a crystal was filtered off and washed with ethyl acetate to obtain 2.3 g of 1-(2-(4-aminopiperidin-1-yl)ethyl)-7-methoxy-1,8-naphthyridin-2(1H)-one hydrochloride as a light yellow solid.

Workup

  1. distillationThe solvent was distilled off under reduced pressure, ethyl acetate
  2. additionwas added to the solid
  3. customthus obtained
  4. filtrationa crystal was filtered off
  5. washwashed with ethyl acetate

Sources & evidence

ORD record
ord-bf0df73e40d844169c41041e424becb0
Source dataset
uspto-grants-2012_07
Patent number
US08211908B2

Reaction notes

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