Piperidine → HCID 19891207, compound

HRID 893861Notes

Reaction equation

HRID 893861 reaction equation
[S:1]1[C:5]23[CH:13]=[CH:12][CH:11]=[CH:10][C:6]2=[N:7][CH:8]=[CH:9][C:4]3=[C:3]([C:14]([OH:16])=O)[CH2:2]1.[NH:17]1[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]1.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=O)C=CC=CC=1.C(N(CC)CC)C>CN(C)C=O.C(OCC)(=O)C>[S:1]1[C:5]23[CH:13]=[CH:12][CH:11]=[CH:10][C:6]2=[N:7][CH:8]=[CH:9][C:4]3=[C:3]([C:14]([N:17]2[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]2)=[O:16])[CH2:2]1

Participants

7

Reactant 4

HCID 8082PiperidineHCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 19891249HCID 19891249, compound

Product 1

HCID 19891207HCID 19891207, compoundYield 85%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

In 5 ml of dimethylformamide were dissolved 458 mg of benzo[b]thieno[2,3-c]pyridine-3-carboxylic acid and 170 mg of piperidine, and 660 mg of DPPA (diphenylphosphorylazide) was added dropwise to the solution under ice-cooling. Then, 335 μl of triethylamine was added to the mixture and the resultant mixture was stirred overnight at room temperature. After the reaction was over, the reaction mixture was diluted with ethyl acetate and the solution was washed with an aqueous 5% citric acid solution, an aqueous 5% sodium hydrogencarbonate solution, and then a saturated aqueous sodium chloride solution and thereafter dried with sodium sulfate. The ethyl acetate layer was concentrated under reduced pressure and the residue was purified by silica gel thin layer chromatography (solvent: chloroform) and then recrystallized from a mixture of chloroform and ether to provide 230 mg (yield of 85%) of 1-(benzo[b]thieno[2,3-c]pyridine-3-carbonyl)-piperidine.

Workup

  1. additionwas added dropwise to the solution under ice-
  2. temperaturecooling
  3. washthe solution was washed with an aqueous 5% citric acid solution
  4. dry with materialan aqueous 5% sodium hydrogencarbonate solution, and then a saturated aqueous sodium chloride solution and thereafter dried with sodium sulfate
  5. concentrationThe ethyl acetate layer was concentrated under reduced pressure
  6. customthe residue was purified by silica gel thin layer chromatography (solvent: chloroform)
  7. customrecrystallized from a mixture of chloroform and ether

Sources & evidence

ORD record
ord-d07c0fe1384a46c6bfd71844c8f0f60a
Source dataset
uspto-grants-1992_06
Patent number
US05126448

Reaction notes

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