Tetrahydrofuran → HCID 86663399, compound

HRID 534884Notes

Reaction equation

HRID 534884 reaction equation
Cl.Cl.[C:3]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[N:13]1[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]1)([CH3:6])([CH3:5])[CH3:4].[Cl:19][C:20]1[N:25]=[CH:24][C:23]([C:26](Cl)=[O:27])=[CH:22][CH:21]=1.C(N(CC)CC)C.O1CCCC1>O>[C:3]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[N:13]1[CH2:18][CH2:17][N:16]([C:26]([C:23]2[CH:24]=[N:25][C:20]([Cl:19])=[CH:21][CH:22]=2)=[O:27])[CH2:15][CH2:14]1)([CH3:6])([CH3:4])[CH3:5]

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 27821656-Chloronicotinoyl ChlorideHCID 667511491-(2-Tert-butylphenyl)piperazine dihydrochloride

Product 1

HCID 86663399HCID 86663399, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 1-(2-tert-butylphenyl)piperazine dihydrochloride obtained in Reference Example 1 (0.5 g), 6-chloropyridine-3-carbonyl chloride (352 mg), triethylamine (0.835 mL), and tetrahydrofuran (30 mL) was stirred at room temperature for over-night. Water was added to the reaction solution, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by flash column chromatography (NH-silica gel, 0:100 hexane/ethyl acetate) to provide the title compound (635 mg, quant.) as a solid.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe ethyl acetate layer was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. customthe residue was purified by flash column chromatography (NH-silica gel, 0:100 hexane/ethyl acetate)

Sources & evidence

ORD record
ord-84a53d0467df48799c0239f813d21167
Source dataset
uspto-grants-2014_10
Patent number
US08853215B2

Reaction notes

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