Hydrochloric Acid → HCID 15115299, compound

HRID 1736048Notes

Reaction equation

HRID 1736048 reaction equation
[N+]([O-])([O-])=O.[Na+].[CH:6]([NH:8][C:9]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)([CH3:18])[CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[C:13](N)[CH:12]=1)=[O:7].O.[OH-].[NH4+].[ClH:28]>S(=O)(=O)(O)O.C(O)(=O)C>[CH:6]([NH:8][C:9]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)([CH3:18])[CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([Cl:28])[CH:12]=1)=[O:7]

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 962WaterHCID 14923Ammonium HydroxideHCID 24268Sodium NitrateHCID 15115298HCID 15115298, compound

Product 1

HCID 15115299HCID 15115299, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 1118Sulfuric AcidSolvent

Procedure

To a solution of N-formyl-1-(3-nitrophenyl)-2-phenyl-2-propylamine (5.0 g, 0.017 mol) in methanol (200 ml) was added 10% Pd/C catalyst (0.5 g) and the mixture hydrogenated at 50 psi in a Parr apparatus for 3 hours. The catalyst was removed by filtration and the solvent evaporated to a white solid, 4.6 g. This solid was recrystallised from isopropanol (50 ml) to give 2.6 g of N-formyl-1-(3-aminophenyl)-2-phenyl-2-propylamine, mp 114°-115° C. To a stirred solution of sodium nitrate (2.0 g, 0.03 mol) in sulphuric acid (15 ml) at 0° C. under nitrogen was added dropwise a solution of N-formyl-1-(3-aminophenyl)-2-phenyl-2-propylamine (7.0 g, 0.027 mol) in acetic acid (75 ml) and the solution was stirred 2.5 hours at a temperature less than 20° C. The above mixture was added to a solution of cuprous chloride (5.3 g, 0.054 mol) in concentrated HCl (50 ml) at 15° C., and the resulting solution was stirred at that temperature for 1 hour. The reaction mixture was poured into water (500 ml), basified with concentrated ammonium hydroxide, and extracted with chloroform (3×200 ml). The combined chloroform extracts were dried over magnesium sulphate and the solvent evaporated to a solid, 7.5 g. This solid was recrystallised from isopropanol (20 ml) to provide 3.2 g of N-formyl-1-(3-chlorophenyl)-2-phenyl-2-propylamine, mp 108°-109° C.

Workup

  1. stirringthe resulting solution was stirred at that temperature for 1 hour
  2. extractionextracted with chloroform (3×200 ml)
  3. dry with materialThe combined chloroform extracts were dried over magnesium sulphate
  4. customthe solvent evaporated to a solid, 7.5 g
  5. customThis solid was recrystallised from isopropanol (20 ml)

Sources & evidence

ORD record
ord-67f9ba6ee84841abb1b4f2517ba5cff0
Source dataset
uspto-grants-1996_07
Patent number
US05539120

Reaction notes

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