Hydrogen Bromide → HCID 22494716, compound

HRID 1816732Notes

Reaction equation

HRID 1816732 reaction equation
N[C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:13][CH2:12][CH:11]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[CH2:10][CH2:9]2)=[CH:4][CH:3]=1.N([O-])=O.[Na+].[BrH:24]>C(O)(=O)C.O.[Cu]Br>[Br:24][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:13][CH2:12][CH:11]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[CH2:10][CH2:9]2)=[CH:4][CH:3]=1

Participants

7

Reactant 3

HCID 260Hydrogen Bromide2×HCID 22494681HCID 22494681, compoundHCID 23668193Sodium Nitrite

Product 1

HCID 22494716HCID 22494716, compound

Reagents, catalysts & solvents 3

HCID 24593copper(I) bromideCatalystHCID 176Acetic AcidSolventHCID 962WaterSolvent2×

Conditions

Temperature
0 °C

Procedure

To a solution of 1-(4-aminophenyl)-4-phenylpiperidine (2 g) in 47% hydrobromic acid (20 ml) and acetic acid (23 ml) was added dropwise sodium nitrite (0.55 g) in water (1 ml) under ice-cooling. The solution was then stirred for 30 minutes at 0° C. The reaction mixture was added dropwise copper(I) bromide (2.27 g) in 47% hydrobromic acid (2.3 ml) under ice-cooling. The reaction mixture was then stirred for 1.5 hours at ambient temperature. The reaction mixture was pulverized with water. The precipitate was collected by filtration. The powder was added 1N-sodium hydroxide (21 ml) and extracted with ethyl acetate. The organic layer was separated, washed with brine, dried over magnesium sulfate. The magnesium sulfate was filtered off, and the filtrate was evaporated under reduced pressure. The residue was purified by column chromatography over silica using dichloromethane/n-hexane (1:1) as the elution to give 1-(4-bromophenyl)-4-phenylpiperidine (1.23 g).

Workup

  1. temperaturecooling
  2. temperaturecooling
  3. stirringThe reaction mixture was then stirred for 1.5 hours at ambient temperature
  4. filtrationThe precipitate was collected by filtration
  5. additionThe powder was added 1N-sodium hydroxide (21 ml)
  6. extractionextracted with ethyl acetate
  7. customThe organic layer was separated
  8. washwashed with brine
  9. dry with materialdried over magnesium sulfate
  10. filtrationThe magnesium sulfate was filtered off
  11. customthe filtrate was evaporated under reduced pressure
  12. customThe residue was purified by column chromatography over silica
  13. washas the elution

Sources & evidence

ORD record
ord-26bd61b627db440e9e1175a8f22709eb
Source dataset
uspto-grants-2005_04
Patent number
US06884868B1

Reaction notes

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