Sodium Hydroxide → 2-Bromo-2-methyl-1-(4-piperidinophenyl)-propan-1-one

HRID 981754Notes

Reaction equation

HRID 981754 reaction equation
[CH3:1][CH:2]([CH3:17])[C:3]([C:5]1[CH:10]=[CH:9][C:8]([N:11]2[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]2)=[CH:7][CH:6]=1)=[O:4].ClS(O)(=O)=O.[Br:23]Br.[OH-].[Na+]>C(O)(=O)C>[Br:23][C:2]([CH3:17])([CH3:1])[C:3]([C:5]1[CH:10]=[CH:9][C:8]([N:11]2[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]2)=[CH:7][CH:6]=1)=[O:4]

Participants

6

Reactant 4

HCID 14798Sodium HydroxideHCID 24408BromineHCID 24638Chlorosulfonic acidHCID 212571912-Methyl-1-(4-(piperidin-1-yl)phenyl)propan-1-one

Product 1

HCID 198795192-Bromo-2-methyl-1-(4-piperidinophenyl)-propan-1-one

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

34.70 g (0.15 mol) of 2-methyl-1-(4-piperidinophenyl)-propan-1-one are dissolved in 200 ml of glacial acetic acid. 0.58 g (5.0 mmol) of chlorosulfonic acid (corresponding to 0.33 ml) are added as catalyst. 24.0 g (0.15 mol) of bromine are then added dropwise at room temperature with thorough stirring in the course of approximately one hour. The solution is then poured onto ice and is brought to about pH 6 with dilute sodium hydroxide solution. The precipitated crystals are extracted with toluene. The toluene solution is dried with Na2SO4 and is concentrated at 40° C. under the vacuum of a rotary evaporator. The slowly crystallising, orange liquid is then reacted further.

Workup

  1. additionThe solution is then poured onto ice
  2. extractionThe precipitated crystals are extracted with toluene
  3. dry with materialThe toluene solution is dried with Na2SO4
  4. concentrationis concentrated at 40° C. under the vacuum of a rotary evaporator
  5. customThe slowly crystallising
  6. customorange liquid is then reacted further

Sources & evidence

ORD record
ord-c6c58e1d63984fa6918fa1968c1987af
Source dataset
uspto-grants-1991_02
Patent number
US04992547

Reaction notes

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