Ethanol hydrochloride → 1-(2-(4-aminopiperidin-1-yl)ethyl)-1,7-naphthyridin-2(1H)-one

HRID 385496Notes

Reaction equation

HRID 385496 reaction equation
[O:1]=[C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][N: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.Cl.C(O)C>C(O)C>[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]=[N:6][CH:5]=3)[CH:10]=[CH:11][C:2]2=[O:1])[CH2:15][CH2:16]1

Participants

4

Reactant 2

HCID 21887872Ethanol hydrochloride2×HCID 57815235tert-butyl (1-(2-(2-oxo-1,7-naphthyridin-1(2H)-yl)ethyl)piperidin-4-yl)carbamate

Product 1

HCID 578152611-(2-(4-aminopiperidin-1-yl)ethyl)-1,7-naphthyridin-2(1H)-oneYield 136.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 2.8 g of tert-butyl (1-(2-(2-oxo-1,7-naphthyridin-1(2H)-yl)ethyl)piperidin-4-yl)carbamate in 20 mL of ethanol, 60 mL of a 6.2 mol/L hydrogen chloride/ethanol solution was added at room temperature, and the mixture was stirred for 2 hours. Thereto was further added 60 mL of a 6.2 mol/L hydrogen chloride/ethanol solution, and the mixture was stirred for 4 hours and then left for 4 days. The solvent was distilled off under reduced pressure, diethyl ether was added to the resultant residue, and the solid was filtered off to obtain 2.8 g of 1-(2-(4-aminopiperidin-1-yl)ethyl)-1,7-naphthyridin-2(1H)-one as a yellow solid.

Workup

  1. stirringthe mixture was stirred for 4 hours
  2. waitleft for 4 days
  3. distillationThe solvent was distilled off under reduced pressure, diethyl ether
  4. additionwas added to the resultant residue
  5. filtrationthe solid was filtered off

Sources & evidence

ORD record
ord-6ba14a7520554e8d84bb3552f9c8be72
Source dataset
uspto-grants-2013_02
Patent number
US08367831B2

Reaction notes

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