Potassium Carbonate → HCID 46178406, compound

HRID 2242523Notes

Reaction equation

HRID 2242523 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([OH:8])[CH:5]=[C:4]([Cl:9])[C:3]=1[N:10]1[CH2:15][CH2:14][N:13]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:12][CH2:11]1.[Cl:23][C:24](Cl)([Cl:28])[CH2:25][CH2:26]Cl.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[Cl:23][C:24]([Cl:28])=[CH:25][CH2:26][O:8][C:6]1[CH:7]=[C:2]([Cl:1])[C:3]([N:10]2[CH2:15][CH2:14][N:13]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:12][CH2:11]2)=[C:4]([Cl:9])[CH:5]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 140561,1,1,3-TetrachloropropaneHCID 58758907HCID 58758907, compound

Product 1

HCID 46178406HCID 46178406, compoundYield 24.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

This compound was prepared in a manner analogous to that of Example 1 Step C, by the reaction of 2.8 grams (0.008 mole) of tert-butyl 4-(2,6-dichloro-4-hydroxyphenyl)piperazinecarboxylate, 2.2 grams (0.012 mole) of 1,1,1,3-tetrachloropropane and 1.7 grams (0.012 mole) of potassium carbonate in 75 mL of DMF. The crude reaction product was purified with column chromatography on silica gel using 50% hexane in methylene chloride and finally 100% methylene chloride as eluants. The appropriate fractions were combined and concentrated under reduced pressure, yielding 0.88 gram of the subject compound. The NMR spectrum was consistent with the proposed structure. The reaction was repeated to obtain additional material for the next reactive step.

Workup

  1. customThis compound was prepared in a manner analogous to that of Example 1 Step C
  2. customThe crude reaction product
  3. customwas purified with column chromatography on silica gel using 50% hexane in methylene chloride and finally 100% methylene chloride as eluants
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-4350a0a1b91d449aa91ae611ce933536
Source dataset
uspto-grants-2010_03
Patent number
US07671201B2

Reaction notes

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