Potassium Carbonate → HCID 19863380, compound

HRID 1164958Notes

Reaction equation

HRID 1164958 reaction equation
[CH3:1][CH:2]1[CH2:7][CH2:6][N:5]([CH2:8][CH2:9][CH2:10][S:11][C:12]2[CH:17]=[CH:16][C:15]([N+:18]([O-])=O)=[CH:14][CH:13]=2)[CH2:4][CH2:3]1.O.O.[Sn](Cl)Cl.C(=O)([O-])[O-].[K+].[K+]>C(O)C.O.C(OCC)(=O)C>[NH2:18][C:15]1[CH:14]=[CH:13][C:12]([S:11][CH2:10][CH2:9][CH2:8][N:5]2[CH2:6][CH2:7][CH:2]([CH3:1])[CH2:3][CH2:4]2)=[CH:17][CH:16]=1

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 61436Stannous chloride dihydrateHCID 19863408HCID 19863408, compound

Product 1

HCID 19863380HCID 19863380, compound

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

Dissolve 15.5 g (0.0520 mol) of 4-methyl-1-[3-[(4-nitrophenyl)thio]propyl]piperidine in 150 mL of ethanol. Add 59.3 g (0.26 mol) of tin(II) chloride dihydrate and heat mixture to reflux for 5 h. After 5 h, cool the reaction mixture to room temperature. Pour reaction mixture over 100 g of potassium carbonate and dilute with 500 mL of water and 500 mL of ethyl acetate. Filter this suspension through celite and separate the layers. Extract the aqueous layer with 3×300 mL of ethyl acetate. Combine organic layers and dry over anhydrous sodium sulfate. Filter the drying agent and remove the solvent in vacuo to provide the title compound.

Workup

  1. temperatureheat mixture
  2. temperatureto reflux for 5 h
  3. additionPour
  4. filtrationFilter this suspension through celite
  5. customseparate the layers
  6. extractionExtract the aqueous layer with 3×300 mL of ethyl acetate
  7. dry with materialCombine organic layers and dry over anhydrous sodium sulfate
  8. filtrationFilter the drying agent
  9. customremove the solvent in vacuo

Sources & evidence

ORD record
ord-4de1bf3bf76d4a4fa9ae7100c49462af
Source dataset
uspto-grants-1990_03
Patent number
US04906634

Reaction notes

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