Water → HCID 77231145, compound

HRID 1526106Notes

Reaction equation

HRID 1526106 reaction equation
[N:1]1([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.C(=O)([O-])[O-].[K+].[K+].[F:20][C:21]1[CH:28]=[C:27](F)[CH:26]=[CH:25][C:22]=1[CH:23]=[O:24].O>CS(C)=O>[F:20][C:21]1[CH:28]=[C:27]([N:4]2[CH2:5][CH2:6][N:1]([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[CH2:2][CH2:3]2)[CH:26]=[CH:25][C:22]=1[CH:23]=[O:24]

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 737702,4-DifluorobenzaldehydeHCID 143452tert-Butyl piperazine-1-carboxylate

Product 1

HCID 77231145HCID 77231145, compoundYield 48.7%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

9.17 g (49.3 mmol) of tert-butyl piperazine-1-carboxylate and then 6.81 g (49.3 mmol) of potassium carbonate, respectively, are added to 7 g (49.3 mmol) of 2,4-difluorobenzaldehyde diluted in 60 ml of dimethylsulfoxide. The solution is carried at 60° C. for 8 hours and then water is added and the product is extracted several times with ethyl acetate. The organic phases are combined, dried on magnesium sulfate and concentrated. The residue obtained is purified by silica gel chromatography (eluent: 7:3 cyclohexane/ethyl acetate) to yield 7.4 g (48%) of tert-butyl 4-(3-fluoro-4-formylphenyl)piperazine-1-carboxylate in the form of a white solid.

Workup

  1. extractionthe product is extracted several times with ethyl acetate
  2. customdried on magnesium sulfate
  3. concentrationconcentrated
  4. customThe residue obtained
  5. customis purified by silica gel chromatography (eluent: 7:3 cyclohexane/ethyl acetate)

Sources & evidence

ORD record
ord-200fde45622c4f6cb15c39dcaa0308db
Source dataset
uspto-grants-2015_07
Patent number
US09085575B2

Reaction notes

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