Potassium Carbonate → HCID 21327230, compound

HRID 2163140Notes

Reaction equation

HRID 2163140 reaction equation
C(O)(=O)/C=C\C(O)=[O:5].[CH3:9][N:10]1[CH2:15][CH:14]=[C:13]([C:16]2[CH:21]=[CH:20][C:19]([CH3:22])=[CH:18][CH:17]=2)[CH2:12][CH2:11]1.[Br-].[Na+].BrBr.C(=O)([O-])[O-].[K+].[K+].[OH-].[Na+]>O.C(Cl)(Cl)Cl>[CH3:9][N:10]1[CH2:11][CH2:12][C:13]2([C:16]3[CH:17]=[CH:18][C:19]([CH3:22])=[CH:20][CH:21]=3)[CH:14]([O:5]2)[CH2:15]1

Participants

8

Reactant 5

HCID 11430Potassium CarbonateHCID 14798Sodium HydroxideHCID 24408BromineHCID 253881Sodium BromideHCID 706089121-Methyl-4-(4-methylphenyl)-1,2,3,6-tetrahydropyridine maleate

Product 1

HCID 21327230HCID 21327230, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolvent3×HCID 6212ChloroformSolvent

Procedure

1-Methyl-4-(4-methylphenyl)-1,2,3,6-tetrahydropyridine maleate (5.0 g, 16.4 mmoles, described in Example 3) is suspended in water (60 ml) and a solution of sodium bromide (5.15 g, 49.9 mmoles) and bromine (0.84 ml) in water (50 ml) is added dropwise to the cooled mixture (<5° C.). The reaction mixture is stirred for 15 min., potassium carbonate (20 g) is added followed by chloroform (100 ml) and a solution of sodium hydroxide pellets (680 mg) in water (10 ml). After stirring vigorously for 15 min., the layers are separated and the aqueous solution is extracted with chloroform. The combined extracts are washed with brine, dried (MgSO4) and evaporated. The residue is triturated with pentane to give the title compound, mp 124°-125.5° C.

Workup

  1. stirringAfter stirring vigorously for 15 min.
  2. customthe layers are separated
  3. extractionthe aqueous solution is extracted with chloroform
  4. washThe combined extracts are washed with brine
  5. dry with materialdried (MgSO4)
  6. customevaporated
  7. customThe residue is triturated with pentane

Sources & evidence

ORD record
ord-257738211a794505a0e7827eccdc91d8
Source dataset
uspto-grants-1979_01
Patent number
US04132710

Reaction notes

Loading…