Sodium Bicarbonate → HCID 57082681, compound

HRID 380496Notes

Reaction equation

HRID 380496 reaction equation
ClC(Cl)(Cl)COC([N:7]1[CH2:12][CH2:11][CH:10]([CH2:13][CH2:14][S:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH2:9][CH2:8]1)=O.C([O-])(O)=O.[Na+]>C(O)(=O)C.[Zn]>[C:16]1([S:15][CH2:14][CH2:13][CH:10]2[CH2:9][CH2:8][NH:7][CH2:12][CH2:11]2)[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1

Participants

5

Reactant 2

HCID 516892Sodium BicarbonateHCID 70214230HCID 70214230, compound

Product 1

HCID 57082681HCID 57082681, compound

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 176Acetic AcidSolvent

Procedure

To a solution of 1.47 g (3.71 mmol) of 1-(2,2,2-trichloroethoxycarbonyl)-4-(2-(phenylmercapto)ethyl)piperidine in 20 mL of glacial acetic acid was heated at 40° C. To this solution was added portionwise 2 g of zinc powder over a period of 1 h with vigorous stirring. After 24 h at 40° C., the reaction mixture was cooled to rt and carefully poured into 250 mL of sat'd NaHCO3 solution. The mixture was extracted 5 times with CH2Cl2 and the combined organic fractions were washed with sat'd NaCl solution, and dried over MgSO4 and filtered. The filtrate was concentrated to give the title compound.

Workup

  1. extractionThe mixture was extracted 5 times with CH2Cl2
  2. washthe combined organic fractions were washed with sat'd NaCl solution
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-012011628ee44ac9987e59c850f60ff4
Source dataset
uspto-grants-2001_10
Patent number
US06303593B1

Reaction notes

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