Water → N-(2-bromoacetyl)-4-(m-chlorophenoxy)piperidine

HRID 463305Notes

Reaction equation

HRID 463305 reaction equation
C(=O)(O)[O-].[Na+].[Br:6][CH2:7][C:8](Br)=[O:9].[Cl:11][C:12]1[CH:13]=[C:14]([CH:22]=[CH:23][CH:24]=1)[O:15][CH:16]1[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]1.O>C(Cl)Cl>[Br:6][CH2:7][C:8]([N:19]1[CH2:18][CH2:17][CH:16]([O:15][C:14]2[CH:22]=[CH:23][CH:24]=[C:12]([Cl:11])[CH:13]=2)[CH2:21][CH2:20]1)=[O:9]

Participants

6

Reactant 4

HCID 962WaterHCID 61147Bromoacetyl bromideHCID 516892Sodium BicarbonateHCID 27353174-(3-Chlorophenoxy)piperidine

Product 1

HCID 20283061N-(2-bromoacetyl)-4-(m-chlorophenoxy)piperidine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a suspension of sodium bicarbonate (34 g, 0.040 mol), 400 ml of methylene chloride and bromoacetyl bromide (15.7 ml, 36.5 g, 0.176 mol) cooled by an ice/salt bath was added dropwise a solution of 4-m-chlorophenoxypiperidine (34.9 g, 0.165 mol) in 400 ml of methylene chloride. The reaction mixture was stirred 1 hour at 0° and 3 hours at room temperature. The reaction mixture was poured into water, extracted with methylene chloride, and the extract was washed with water, 3N HCl, saturated sodium bicarbonate and saturated sodium chloride. Evaporation of the solvent provided N-(2-bromoacetyl)-4-(m-chlorophenoxy)piperidine.

Workup

  1. temperaturecooled by an ice/salt bath
  2. extractionextracted with methylene chloride
  3. washthe extract was washed with water, 3N HCl, saturated sodium bicarbonate and saturated sodium chloride
  4. customEvaporation of the solvent

Sources & evidence

ORD record
ord-53af66871a3047d6aa16c19e55c75473
Source dataset
uspto-grants-1985_05
Patent number
US04518713

Reaction notes

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