Hydrogen chloride-ethyl acetate → N-[1-(phenylaminocarbonylmethyl)piperidin-4-ylmethyl]-5-thia-1,8b-diazaacenaphthylene-4-carboxamide dihydrochloride

HRID 1978470Notes

Reaction equation

HRID 1978470 reaction equation
[C:1]1([NH:7][C:8]([CH2:10][N:11]2[CH2:16][CH2:15][CH:14]([CH2:17][NH:18][C:19]([C:21]3[S:31][C:30]4[N:32]5[C:23](=[CH:24][N:25]=[C:26]5[CH:27]=[CH:28][CH:29]=4)[CH:22]=3)=[O:20])[CH2:13][CH2:12]2)=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[ClH:33].C(OCC)(=O)C>C(Cl)(Cl)Cl.CO>[ClH:33].[ClH:33].[C:1]1([NH:7][C:8]([CH2:10][N:11]2[CH2:16][CH2:15][CH:14]([CH2:17][NH:18][C:19]([C:21]3[S:31][C:30]4[N:32]5[C:23](=[CH:24][N:25]=[C:26]5[CH:27]=[CH:28][CH:29]=4)[CH:22]=3)=[O:20])[CH2:13][CH2:12]2)=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 21866389Hydrogen chloride-ethyl acetateHCID 70246692N-[1-(phenylaminocarbonylmethyl)-piperidin-4-ylmethyl]-5-thia-1,8b-diazaacenaphthylene-4-carboxamide

Product 1

HCID 70248335N-[1-(phenylaminocarbonylmethyl)piperidin-4-ylmethyl]-5-thia-1,8b-diazaacenaphthylene-4-carboxamide dihydrochlorideYield 60%

Reagents, catalysts & solvents 1

HCID 21584188Chloroform methanolSolvent

Procedure

To a solution of N-[1-(phenylaminocarbonylmethyl)-piperidin-4-ylmethyl]-5-thia-1,8b-diazaacenaphthylene-4-carboxamide in chloroform-methanol (1:1) was added 2 ml (8.0 mM) of 4N-HCl/ethyl acetate. The solvent was distilled off under reduced pressure and the residue was diluted with ethanol/ether ({fraction (1/10)}). The resulting crystals were collected by filtration and rinsed with ethanol and diethyl ether to provide the title compound as orange-colored crystals (506 mg, 60%).

Workup

  1. distillationThe solvent was distilled off under reduced pressure
  2. additionthe residue was diluted with ethanol/ether ({fraction (1/10)})
  3. filtrationThe resulting crystals were collected by filtration
  4. washrinsed with ethanol and diethyl ether

Sources & evidence

ORD record
ord-fc229b3bdf074c29872b73ff96cc0563
Source dataset
uspto-grants-2001_05
Patent number
US06235731B1

Reaction notes

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