Hydrochloric Acid → HCID 18423040, compound

HRID 1282071Notes

Reaction equation

HRID 1282071 reaction equation
N([O-])=O.[Na+].N[C:6]1[CH:11]=[C:10]([CH2:12][N:13]2[CH2:18][CH2:17][N:16]([C:19]3[CH:24]=[CH:23][C:22]([F:25])=[CH:21][CH:20]=3)[CH2:15][CH2:14]2)[CH:9]=[CH:8][C:7]=1[CH2:26][NH:27][C:28](=[O:30])[CH3:29].[OH-].[Na+].[ClH:33]>[Cu]Cl>[Cl:33][C:6]1[CH:11]=[C:10]([CH2:12][N:13]2[CH2:18][CH2:17][N:16]([C:19]3[CH:24]=[CH:23][C:22]([F:25])=[CH:21][CH:20]=3)[CH2:15][CH2:14]2)[CH:9]=[CH:8][C:7]=1[CH2:26][NH:27][C:28](=[O:30])[CH3:29]

Participants

6

Reactant 4

HCID 313Hydrochloric Acid2×HCID 14798Sodium HydroxideHCID 18423147HCID 18423147, compoundHCID 23668193Sodium Nitrite

Product 1

HCID 18423040HCID 18423040, compound

Reagents, catalysts & solvents 1

HCID 62652Cuprous chlorideCatalyst

Procedure

To an aqueous solution (2 ml) of sodium nitrite (213 mg) was added a solution of N-(2-amino-4-((4-(4-fluorophenyl)piperazin-1-yl)methyl)phenylmethyl)acetamide (1.1 g) in conc. hydrochloric acid (5 ml) under ice-cooling. This mixture was stirred at the same temperature for 40 min. The reaction mixture was added to a solution of copper(I) chloride (183 mg) in conc. hydrochloric acid (2 ml) over 10 min. The mixture was stirred at room temperature for 2 hr. The reaction mixture was poured into aqueous sodium hydroxide solution and extracted with ethyl acetate. The extract was washed with saturated brine and dried over anhydrous sodium sulfate. The solvent was evaporated to give a green oil (1.4 g). The obtained green oil was purified by silica gel column chromatography (developing solvent ; chloroform:methanol=20:1) to give a pale-brown solid (0.9 g). This pale-brown solid was crystallized from ethyl acetate/hexane to give the title compound (0.75 g) as yellow crystals.

Workup

  1. temperaturecooling
  2. stirringThe mixture was stirred at room temperature for 2 hr
  3. extractionextracted with ethyl acetate
  4. washThe extract was washed with saturated brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. customThe solvent was evaporated

Sources & evidence

ORD record
ord-b0fb6e9b81b34b3eac0bcfae47d7671a
Source dataset
uspto-grants-2002_09
Patent number
US06455528B1

Reaction notes

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