Potassium Hydroxide → HCID 28556555, compound

HRID 1158211Notes

Reaction equation

HRID 1158211 reaction equation
[CH:1]1([NH:7][C:8]2[CH:13]=[CH:12][C:11]([CH3:14])=[CH:10][CH:9]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[Br:15]Br.[OH-].[K+]>C(Cl)Cl>[Br:15][C:9]1[CH:10]=[C:11]([CH3:14])[CH:12]=[CH:13][C:8]=1[NH:7][CH:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 14797Potassium HydroxideHCID 24408BromineHCID 11424045N-cyclohexyl-4-methylaniline

Product 1

HCID 28556555HCID 28556555, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

In a 100-mL flask, N-cyclohexyl-4-methylaniline (2.00 g, 10.6 mmol) was dissolved in methylene chloride (20 mL) and a solution of bromine (Br2) (1.69 g, 10.6 mmol) dissolved in methylene chloride (16 ml) was injected at 0° C. for 30 minutes. Then, the solution was further stirred for 2 hours, and a 1 N aqueous KOH (20 mL) solution was added. The solution added with the aqueous solution was transferred to a separatory funnel and extracted from methylene chloride (40 mL) twice. Water was removed from the combined organic layer over MgSO4, and filtered with a glass filter. The rotary evaporator was used to remove the solvent, thereby obtaining a residue. The obtained residue was separated by column chromatography to obtain colorless oil (2.67 g, 94%).

Workup

  1. additionThe solution added with the aqueous solution
  2. customwas transferred to a separatory funnel
  3. extractionextracted from methylene chloride (40 mL) twice
  4. customWater was removed from the combined organic layer over MgSO4
  5. filtrationfiltered with a glass
  6. filtrationfilter
  7. customThe rotary evaporator
  8. customto remove the solvent
  9. customobtaining a residue
  10. customThe obtained residue was separated by column chromatography

Sources & evidence

ORD record
ord-7b997fe2f8e846fe8071d51490e814f6
Source dataset
uspto-grants-2010_10
Patent number
US07807762B2

Reaction notes

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