Hydrogen chloride-ethyl acetate → HCID 68928882, compound

HRID 385634Notes

Reaction equation

HRID 385634 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](=[N:33][CH:34]=[CH: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](=[N:33][CH:34]=[CH: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 57815511tert-butyl (2,3-dihydro-1,4-benzodioxin-6-ylmethyl)(1-(2-(2-oxo-1,5-naphthyridin-1(2H)-yl)ethyl)piperidin-4-yl)carbamate

Product 1

HCID 68928882HCID 68928882, compound

Procedure

To 0.69 g of tert-butyl (2,3-dihydro-1,4-benzodioxin-6-ylmethyl)(1-(2-(2-oxo-1,5-naphthyridin-1(2H)-yl)ethyl)piperidin-4-yl)carbamate, 25 mL of a 4 mol/L hydrogen chloride/ethyl acetate solution was added, and the mixture was stirred at room temperature for 42 hours. The solvent was distilled off under reduced pressure, a mixed solution of ethyl acetate and ethanol (5:1) was added to the resultant residue, and the solid was filtered off to obtain 0.59 g of 1-(2-(4-((2,3-dihydro-1,4-benzodioxin-6-ylmethyl)amino)piperidin-1-yl)ethyl)-1,5-naphthyridin-2(1H)-one hydrochloride as a light yellow solid.

Workup

  1. distillationThe solvent was distilled off under reduced pressure
  2. additiona mixed solution of ethyl acetate and ethanol (5:1) was added to the resultant residue
  3. filtrationthe solid was filtered off

Sources & evidence

ORD record
ord-35080dc7dc8142f1a08050aea1e5b4d4
Source dataset
uspto-grants-2013_02
Patent number
US08367831B2

Reaction notes

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