Hydrochloric Acid → HCID 58625125, compound

HRID 1968833Notes

Reaction equation

HRID 1968833 reaction equation
Cl.O.[CH:3]1([CH2:9][NH:10][C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([O:17][C:18]3[CH:23]=[CH:22][C:21]([N+:24]([O-:26])=[O:25])=[C:20]([CH:27](OC)[O:28]C)[CH:19]=3)[CH:12]=2)[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4]1>C1COCC1>[CH:3]1([CH2:9][NH:10][C:11]2[CH:12]=[C:13]([CH:14]=[CH:15][CH:16]=2)[O:17][C:18]2[CH:23]=[CH:22][C:21]([N+:24]([O-:26])=[O:25])=[C:20]([CH:19]=2)[CH:27]=[O:28])[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 962Water2×HCID 58625082HCID 58625082, compound

Product 1

HCID 58625125HCID 58625125, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

12N HCl (2 mL) and H2O (4 mL) were added to a mixture of cyclohexylmethyl-[3-(3-dimethoxymethyl-4-nitro-phenoxy)-phenyl]-amine (0.0055 mol) in THF (17 mL), and the reaction mixture was stirred overnight at room temperature. H2O was added, and the mixture was extracted with diisopropyl ether. The organic layer was washed with a 10% NaHCO3 solution, dried (MgSO4), filtered off and the solvent was evaporated. The residue was purified by short column chromatography (eluent: 100% CH2Cl2). The purest product fractions were collected and the solvent was evaporated to yield the title compound as a residue.

Workup

  1. extractionthe mixture was extracted with diisopropyl ether
  2. washThe organic layer was washed with a 10% NaHCO3 solution
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered off
  5. customthe solvent was evaporated
  6. customThe residue was purified by short column chromatography (eluent: 100% CH2Cl2)
  7. customThe purest product fractions were collected
  8. customthe solvent was evaporated

Sources & evidence

ORD record
ord-11455c7f375b447b89c53e8e52fa02d4
Source dataset
uspto-grants-2013_04
Patent number
US08426429B2

Reaction notes

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