Hydrogen chloride-ethyl acetate → 1-(2-(4-((2,3-dihydro-1,4-benzodioxin-6-ylmethyl)amino)piperidin-1-yl)ethyl)-1,8-naphthyridin-2(1H)-one hydrochloride

HRID 385625Notes

Reaction equation

HRID 385625 reaction equation
[O:1]1[C:6]2[CH:7]=[CH:8][C:9]([CH2:11][N:12]([CH:20]3[CH2:25][CH2:24][N:23]([CH2:26][CH2:27][N:28]4[C:37]5[C:32](=[CH:33][CH:34]=[CH:35][N:36]=5)[CH:31]=[CH:30][C:29]4=[O:38])[CH2:22][CH2:21]3)C(=O)OC(C)(C)C)=[CH:10][C:5]=2[O:4][CH2:3][CH2:2]1.[ClH:39].C(OCC)(=O)C>>[ClH:39].[O:1]1[C:6]2[CH:7]=[CH:8][C:9]([CH2:11][NH:12][CH:20]3[CH2:25][CH2:24][N:23]([CH2:26][CH2:27][N:28]4[C:37]5[C:32](=[CH:33][CH:34]=[CH:35][N:36]=5)[CH:31]=[CH:30][C:29]4=[O:38])[CH2:22][CH2:21]3)=[CH:10][C:5]=2[O:4][CH2:3][CH2:2]1

Participants

3

Reactant 2

HCID 21866389Hydrogen chloride-ethyl acetateHCID 57815442tert-butyl (2,3-dihydro-1,4-benzodioxin-6-ylmethyl)(1-(2-(2-oxo-1,8-naphthyridin-1(2H)-yl)ethyl)piperidin-4-yl)carbamate

Product 1

HCID 248668681-(2-(4-((2,3-dihydro-1,4-benzodioxin-6-ylmethyl)amino)piperidin-1-yl)ethyl)-1,8-naphthyridin-2(1H)-one hydrochloride

Procedure

To 1.4 g of tert-butyl (2,3-dihydro-1,4-benzodioxin-6-ylmethyl)(1-(2-(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 1 day. The solvent was distilled off under reduced pressure, thereto was added ethanol, and the solvent was distilled off under reduced pressure. Ethyl acetate was added to the resultant residue, and after stirring, the solid was filtered off to obtain 1.2 g of 1-(2-(4-((2,3-dihydro-1,4-benzodioxin-6-ylmethyl)amino)piperidin-1-yl)ethyl)-1,8-naphthyridin-2(1H)-one hydrochloride as a white solid.

Workup

  1. distillationThe solvent was distilled off under reduced pressure
  2. additionwas added ethanol
  3. distillationthe solvent was distilled off under reduced pressure
  4. additionEthyl acetate was added to the resultant residue
  5. stirringafter stirring
  6. filtrationthe solid was filtered off

Sources & evidence

ORD record
ord-ed2333b3332b4396a112cb56aeeba242
Source dataset
uspto-grants-2013_02
Patent number
US08367831B2

Reaction notes

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