Hydrochloric Acid → HCID 53635745, compound

HRID 395675Notes

Reaction equation

HRID 395675 reaction equation
[CH3:1][O:2][C:3]1[CH:33]=[CH:32][C:6]([C:7]([NH:9][C:10]2[C:11]([NH:16][C:17]([CH:19]3[CH2:24][CH2:23][N:22](CC4C=CC=CC=4)[CH2:21][CH2:20]3)=[O:18])=[CH:12][CH:13]=[CH:14][CH:15]=2)=[O:8])=[CH:5][CH:4]=1.Cl>C(O)C>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([C:7]([NH:9][C:10]2[C:11]([NH:16][C:17]([CH:19]3[CH2:20][CH2:21][NH:22][CH2:23][CH2:24]3)=[O:18])=[CH:12][CH:13]=[CH:14][CH:15]=2)=[O:8])=[CH:32][CH:33]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 9824675HCID 9824675, compound

Product 1

HCID 53635745HCID 53635745, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of N1-(4-methoxybenzoyl)-N2-(1-benzylpiperidin-4-ylcarbonyl)-1,2-benzenediamine (1.02 g, 2.30 †mmol), 1 N aqueous hydrochloric acid (5 mL), and 5% pallidium-on-carbon (1.06 g) in ethanol (100 mL) was placed under a hydrogen atmosphere (1 bar). After 16 h, the mixture was filtered through diatomaceous earth and the filtrate concentrated in vacuo. The residue was treated with 1 N aqueous sodium hydroxide followed by ethyl acetate. The aqueous layer was extracted twice with ethyl acetate and the combined organics were washed with 1 N aqueous sodium hydroxide, saturated sodium chloride solution, and dried (potassium carbonate). Concentration and recrystallization yielded 656 mg (81%) of the title compound.

Workup

  1. filtrationthe mixture was filtered through diatomaceous earth
  2. concentrationthe filtrate concentrated in vacuo
  3. additionThe residue was treated with 1 N aqueous sodium hydroxide
  4. extractionThe aqueous layer was extracted twice with ethyl acetate
  5. washthe combined organics were washed with 1 N aqueous sodium hydroxide, saturated sodium chloride solution
  6. dry with materialdried (potassium carbonate)
  7. concentrationConcentration and recrystallization

Sources & evidence

ORD record
ord-d1551d62dae542f3aeed65c909e342e9
Source dataset
uspto-grants-2003_08
Patent number
US06605626B2

Reaction notes

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