Hydrogen chloride-ethyl acetate → 1-(2-(4-((2,3-dihydro-1,4-benzodioxin-6-ylmethyl)amino)piperidin-1-yl)ethyl)-1,7-naphthyridin-2(1H)-one hydrochloride

HRID 385630Notes

Reaction equation

HRID 385630 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]=[N:35][CH: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]=[N:35][CH: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 57815476HCID 57815476, compound

Product 1

HCID 689271531-(2-(4-((2,3-dihydro-1,4-benzodioxin-6-ylmethyl)amino)piperidin-1-yl)ethyl)-1,7-naphthyridin-2(1H)-one hydrochloride

Procedure

To 0.15 g of tert-butyl (2,3-dihydro-1,4-benzodioxin-6-ylmethyl)(1-(2-(2-oxo-1,7-naphthyridin-1(2H)-yl)ethyl)piperidin-4-yl)carbamate, 8 mL of a 4 mol/L hydrogen chloride/ethyl acetate solution was added, the mixture was reacted at room temperature for 21 hours, and the solvent was distilled off under reduced pressure. Ethanol was added to the resultant residue, the solvent was distilled off under reduced pressure, ethyl acetate was then added to the resultant residue, and the solid was filtered off to obtain 0.15 g of 1-(2-(4-((2,3-dihydro-1,4-benzodioxin-6-ylmethyl)amino)piperidin-1-yl)ethyl)-1,7-naphthyridin-2(1H)-one hydrochloride as a yellow solid.

Workup

  1. customthe mixture was reacted at room temperature for 21 hours
  2. distillationthe solvent was distilled off under reduced pressure
  3. additionEthanol was added to the resultant residue
  4. distillationthe solvent was distilled off under reduced pressure, ethyl acetate
  5. additionwas then added to the resultant residue
  6. filtrationthe solid was filtered off

Sources & evidence

ORD record
ord-2b1b0a4532864f78955bdf086fb5a3ba
Source dataset
uspto-grants-2013_02
Patent number
US08367831B2

Reaction notes

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