Tetrahydrofuran → HCID 58243583, compound

HRID 389107Notes

Reaction equation

HRID 389107 reaction equation
[CH2:1]([N:3]=[C:4]=[S:5])[CH3:2].[NH:6]1[CH2:11][CH2:10][CH:9]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH2:8][CH2:7]1.[CH2:17]1COCC1>>[CH2:1]([N:3]=[C:4]([S:5][CH3:17])[N:6]1[CH2:11][CH2:10][CH:9]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH2:8][CH2:7]1)[CH3:2]

Participants

4

Reactant 3

HCID 8028TetrahydrofuranHCID 10966Ethyl isothiocyanateHCID 70770Ethyl 4-piperidinecarboxylate

Product 1

HCID 58243583HCID 58243583, compound

Procedure

Ethyl isothiocyanate (0.60 ml) was added to a solution of ethyl piperidine-4-carboxylate (1.02 g) in THF (20 ml), followed by stirring at room temperature for one hour. The reaction solution was concentrated and the resulting colorless oily product was made into an ethanol solution (20 ml), iodomethane (2.0 ml) was added thereto, followed by stirring at 60° C. for 3 hours. The reaction solution was concentrated, an aqueous saturated sodium hydrogen carbonate solution was added thereto, followed by extraction with chloroform, the organic layer was washed with saturated brine and was dried over anhydrous magnesium sulfate, and the solvent was evaporated to obtain ethyl 1-[(ethylimino)(methylsulfanyl)methyl]piperidine-4-carboxylate (1.84 g) as a light yellow oily product.

Workup

  1. concentrationThe reaction solution was concentrated
  2. additionwas added
  3. stirringby stirring at 60° C. for 3 hours
  4. concentrationThe reaction solution was concentrated
  5. additionan aqueous saturated sodium hydrogen carbonate solution was added
  6. extractionfollowed by extraction with chloroform
  7. washthe organic layer was washed with saturated brine
  8. dry with materialwas dried over anhydrous magnesium sulfate
  9. customthe solvent was evaporated

Sources & evidence

ORD record
ord-995a44d6bc3c470fad3e82960f2ac9bb
Source dataset
uspto-grants-2013_02
Patent number
US08377923B2

Reaction notes

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