Ethyl 4-piperidinecarboxylate → Ethyl 1-carbamothioylpiperidine-4-carboxylate

HRID 1028145Notes

Reaction equation

HRID 1028145 reaction equation
[Si]([N:5]=[C:6]=[S:7])(C)(C)C.[NH:8]1[CH2:13][CH2:12][CH:11]([C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH2:10][CH2:9]1>O1CCCC1.C(OCC)(=O)C>[C:6]([N:8]1[CH2:13][CH2:12][CH:11]([C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH2:10][CH2:9]1)(=[S:7])[NH2:5]

Participants

5

Reactant 2

HCID 70770Ethyl 4-piperidinecarboxylateHCID 75297Isothiocyanatotrimethylsilane

Product 1

HCID 23076419Ethyl 1-carbamothioylpiperidine-4-carboxylateYield 20.3%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of TMS-isothiocyanate (5.4 mL, 38 mmol) and ethyl piperidine-4-carboxylate (5.9 ml, 38 mmol) in tetrahydrofuran (127 ml) was stirred at room temperature for 3 days. The mixture was then diluted with 500 mL ethyl acetate and washed with 500 mL water and 500 mL brine. The aqueous fractions were further extracted with 500 mL ethyl acetate. The combined organic extracts were dried over sodium sulfate and concentrated under reduced pressure. The residue was purified by CombiFlash (40-100% ethyl acetate/hexanes) to provide 1.85 g (7.7 mmol, 20%) of ethyl 1-carbamothioylpiperidine-4-carboxylate as a white solid.

Workup

  1. washwashed with 500 mL water and 500 mL brine
  2. extractionThe aqueous fractions were further extracted with 500 mL ethyl acetate
  3. dry with materialThe combined organic extracts were dried over sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by CombiFlash (40-100% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-46960106a52a4a48b1398f104ccdfe19
Source dataset
uspto-grants-2014_05
Patent number
US08735417B2

Reaction notes

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