Water → Ethyl 1-(3-phenyl-1,2,4-thiadiazol-5-yl)piperidine-4-carboxylate

HRID 2263362Notes

Reaction equation

HRID 2263362 reaction equation
[NH:1]1[CH2:11][CH2:10][CH:4]([C:5]([O:7][CH2:8][CH3:9])=[O:6])[CH2:3][CH2:2]1.Cl[C:13]1[S:17][N:16]=[C:15]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[N:14]=1.C(N(CC)CC)C.O>CN(C)C=O>[C:18]1([C:15]2[N:14]=[C:13]([N:1]3[CH2:2][CH2:3][CH:4]([C:5]([O:7][CH2:8][CH3:9])=[O:6])[CH2:10][CH2:11]3)[S:17][N:16]=2)[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 322625-Chloro-3-phenyl-1,2,4-thiadiazoleHCID 70770Ethyl 4-piperidinecarboxylate

Product 1

HCID 68779858Ethyl 1-(3-phenyl-1,2,4-thiadiazol-5-yl)piperidine-4-carboxylateYield 75.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixed solution of ethyl isonipecotate (0.782 ml, 5.08 mmol), 5-chloro-3-phenyl-1,2,4-thiadiazole (1.00 g, 5.08 mmol) and triethylamine (0.708 ml, 5.08 mmol) in N,N-dimethylformamide (10 ml) was stirred at room temperature for 30 minutes. The reaction mixture was poured to water and extracted with ethyl acetate. The extract was washed with water and dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. The residue was recrystallized from a mixed solvent of hexane and ethyl acetate to yield 1.22 g (75.8%) of the desired product.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe extract was washed with water
  3. dry with materialdried over anhydrous magnesium sulfate
  4. distillationthe solvent was distilled off under reduced pressure
  5. customThe residue was recrystallized from a mixed solvent of hexane and ethyl acetate

Sources & evidence

ORD record
ord-48be604d3c024e7288af592edde54e2e
Source dataset
uspto-grants-2010_12
Patent number
US07851473B2

Reaction notes

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