Phosphorus tribromide → 1-[4-(2-Bromoethyl)piperidin-1-yl]-2,2-diphenylethanone

HRID 2370934Notes

Reaction equation

HRID 2370934 reaction equation
O[CH2:2][CH2:3][CH:4]1[CH2:9][CH2:8][N:7]([C:10](=[O:24])[CH:11]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH2:6][CH2:5]1.P(Br)(Br)[Br:26]>ClCCl>[Br:26][CH2:2][CH2:3][CH:4]1[CH2:9][CH2:8][N:7]([C:10](=[O:24])[CH:11]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH2:6][CH2:5]1

Participants

4

Reactant 2

HCID 24614Phosphorus tribromideHCID 582303821-[4-(2-Hydroxyethyl)piperidin-1-yl]-2,2-diphenylethanone

Product 1

HCID 674160211-[4-(2-Bromoethyl)piperidin-1-yl]-2,2-diphenylethanoneYield 26.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1-[4-(2-Hydroxyethyl)piperidin-1-yl]-2,2-diphenylethanone (2.39 g; 8.11 mmol) was dissolved in dichloromethane (20 ml). At room temperature, phosphorous tribromide (1.6 ml; 8.92 mmol) was slowly added dropwise. The reaction mixture was heated under reflux for 4 h. Cooling was followed by washing with saturated NaHCO3 solution, 2N HCl and saturated NaCl solution, and the organic phase was separated off and dried over Na2SO4. The solvent was removed under reduced pressure. Purification of the residue through a cartridge (silica gel) resulted in 1-[4-(2-bromoethyl)-piperidin-1-yl]-2,2-diphenylethanone (0.75 g; 2.13 mmol).

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureunder reflux for 4 h
  3. temperatureCooling
  4. washby washing with saturated NaHCO3 solution, 2N HCl and saturated NaCl solution
  5. customthe organic phase was separated off
  6. dry with materialdried over Na2SO4
  7. customThe solvent was removed under reduced pressure
  8. customPurification of the residue through a cartridge (silica gel)

Sources & evidence

ORD record
ord-4274a8b147194b55bf55472c0d4dc76f
Source dataset
uspto-grants-2014_04
Patent number
US08710232B2

Reaction notes

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