Piperidine → (1-Thiocarbamoylpiperidin-4-yl)acetic acid tert-butyl ester

HRID 1716516Notes

Reaction equation

HRID 1716516 reaction equation
[C:1]([O:5][C:6](=[O:14])[CH2:7][CH:8]1[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2].C1C2C(COC([N:32]=[C:33]=[S:34])=O)C3C(=CC=CC=3)C=2C=CC=1.N1CCCCC1>C(Cl)(Cl)Cl>[C:1]([O:5][C:6](=[O:14])[CH2:7][CH:8]1[CH2:13][CH2:12][N:11]([C:33](=[S:34])[NH2:32])[CH2:10][CH2:9]1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 8082PiperidineHCID 4154759Fmoc isothiocyanateHCID 23511620Tert-butyl 2-(piperidin-4-yl)acetate

Product 1

HCID 58706572(1-Thiocarbamoylpiperidin-4-yl)acetic acid tert-butyl ester

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

A solution of piperidin-4-ylacetic acid tert-butyl ester (10.72 g, 50.0 mmol) in chloroform (100 ml) was added to a solution of 9-fluorenylmethoxycarbonyl isothiocyanate (14.07 g, 50.0 mmol) in chloroform (100 ml) and the mixture was stirred at room temperature for 1 hour. Then, piperidine (80 ml) was added and the mixture was stirred at room temperature for 30 minutes. After the reaction solution was concentrated, water was added, and it was extracted with ethyl acetate and washed with a saturated brine. The organic layer was dried over magnesium sulfate and the residue obtained by vacuum concentration was washed with isopropyl ether and the title compound was obtained (11.35 g, 98%).

Workup

  1. stirringthe mixture was stirred at room temperature for 30 minutes
  2. concentrationAfter the reaction solution was concentrated
  3. additionwater was added
  4. extractionit was extracted with ethyl acetate
  5. washwashed with a saturated brine
  6. dry with materialThe organic layer was dried over magnesium sulfate
  7. customthe residue obtained by vacuum concentration
  8. washwas washed with isopropyl ether

Sources & evidence

ORD record
ord-0ca6a52373b042fbb4b75bbd76010b49
Source dataset
uspto-grants-2010_09
Patent number
US07803801B2

Reaction notes

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