Water → 1-(2-Bromoacetyl)-4-(4-ethylphenoxy)piperidine

HRID 463326Notes

Reaction equation

HRID 463326 reaction equation
[Br:1][CH2:2][C:3](Br)=[O:4].C(=O)(O)[O-].[Na+].[CH2:11]([C:13]1[CH:25]=[CH:24][C:16]([O:17][CH:18]2[CH2:23][CH2:22][NH:21][CH2:20][CH2:19]2)=[CH:15][CH:14]=1)[CH3:12].O>ClCCl>[Br:1][CH2:2][C:3]([N:21]1[CH2:22][CH2:23][CH:18]([O:17][C:16]2[CH:24]=[CH:25][C:13]([CH2:11][CH3:12])=[CH:14][CH:15]=2)[CH2:19][CH2:20]1)=[O:4]

Participants

6

Reactant 4

HCID 962WaterHCID 61147Bromoacetyl bromideHCID 516892Sodium BicarbonateHCID 134574294-(4-Ethylphenoxy)piperidine

Product 1

HCID 202831151-(2-Bromoacetyl)-4-(4-ethylphenoxy)piperidineYield 96.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a stirred suspension of 6.03 ml (69.3 mmol) of bromoacetyl bromide, 13.0 g (155 mmol) of sodium bicarbonate and 160 ml of dry dichloromethane in an ice bath was added dropwise a solution of 13.0 g (63.4 mmol) of 4-(4-ethylphenoxy)piperidine in 140 ml of dry dichloromethane. The mixture was stirred 1 hour at 0° and 45 minutes at room temperature. The mixture was subsequently poured into water, extracted twice with dichloromethane, washed with saturated sodium chloride and dried over potassium carbonate. Filtration followed by evaporation of the solvent provided 20.0 g (61.3 mmol) of 1-(2-bromoacetyl)-4-(4-ethylphenoxy)piperidine as an oil.

Workup

  1. extractionextracted twice with dichloromethane
  2. washwashed with saturated sodium chloride
  3. dry with materialdried over potassium carbonate
  4. filtrationFiltration
  5. customfollowed by evaporation of the solvent

Sources & evidence

ORD record
ord-e42d91b4c432488c8cdb8b11af37204e
Source dataset
uspto-grants-1985_05
Patent number
US04518713

Reaction notes

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