Hydrogen chloride-ethyl acetate → N-[1-[(thiazol-4-yl)methyl]piperidin-4-ylmethyl]-5-thia-1,8b-diazaacenaphthylene-4-carboxamide Trihydrochloride

HRID 1978459Notes

Reaction equation

HRID 1978459 reaction equation
[S:1]1[CH:5]=[C:4]([CH2:6][N:7]2[CH2:12][CH2:11][CH:10]([CH2:13][NH:14][C:15]([C:17]3[S:27][C:26]4[N:28]5[C:19](=[CH:20][N:21]=[C:22]5[CH:23]=[CH:24][CH:25]=4)[CH:18]=3)=[O:16])[CH2:9][CH2:8]2)[N:3]=[CH:2]1.[ClH:29].C(OCC)(=O)C>C(O)C>[ClH:29].[ClH:29].[ClH:29].[S:1]1[CH:5]=[C:4]([CH2:6][N:7]2[CH2:8][CH2:9][CH:10]([CH2:13][NH:14][C:15]([C:17]3[S:27][C:26]4[N:28]5[C:19](=[CH:20][N:21]=[C:22]5[CH:23]=[CH:24][CH:25]=4)[CH:18]=3)=[O:16])[CH2:11][CH2:12]2)[N:3]=[CH:2]1

Participants

4

Reactant 2

HCID 21866389Hydrogen chloride-ethyl acetateHCID 21993714N-(1-[(thiazol-4-yl)methyl]piperidin-4-ylmethyl]-5-thia-1,8b-diazaacenaphthylene-4-carboxamide

Product 1

HCID 21994197N-[1-[(thiazol-4-yl)methyl]piperidin-4-ylmethyl]-5-thia-1,8b-diazaacenaphthylene-4-carboxamide TrihydrochlorideYield 28%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of N-[1-[(thiazol-4-yl)methyl]piperidin-4-ylmethyl]-5-thia-1,8b-diazaacenaphthylene-4-carboxamide in ethanol 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 ether. The crystals that formed were harvested by filtration and rinsed with ethanol and diethyl ether to provide the title compound as orange-colored crystals (150 mg, 28%).

Workup

  1. distillationThe solvent was distilled off under reduced pressure
  2. additionthe residue was diluted with ether
  3. customThe crystals that formed
  4. filtrationwere harvested by filtration
  5. washrinsed with ethanol and diethyl ether

Sources & evidence

ORD record
ord-2ddab0d055624d3a97c86614a726e537
Source dataset
uspto-grants-2001_05
Patent number
US06235731B1

Reaction notes

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