ChemicalBook CAS DataBase List benzyl 4-[amino(thiocarbonyl)]piperidine-1-carboxylate

benzyl 4-[amino(thiocarbonyl)]piperidine-1-carboxylate synthesis

6synthesis methods

Product Name:benzyl 4-[amino(thiocarbonyl)]piperidine-1-carboxylate
CAS Number:167757-46-2
Molecular formula:C14H18N2O2S
Molecular Weight:278.37

BENZYL 4-(AMINOCARBONYL)TETRAHYDRO-1(2H)-PYRIDINECARBOXYLATE

167757-45-1
98 suppliers
$22.00/1g

benzyl 4-[amino(thiocarbonyl)]piperidine-1-carboxylate

167757-46-2
22 suppliers
$187.33/1gm:

Yield:167757-46-2 23%

Reaction Conditions:

with Lawessons reagent in tetrahydrofuran; for 4 h;

Steps:

4 Benzyl-4-carbamothioylpiperidine-1-carboxylate, cmpd. of formula 8 [R1=1-benzyloxycarbonyl-piperidin-4-yl]

Benzyl-4-carbamothioylpiperidine-1-carboxylate, cmpd. of formula 8 [R1=1-benzyloxycarbonyl-piperidin-4-yl]
Benzyl-4-carbamoylpiperidine-1-carboxylate (7.5 g, 38.6 mmol) was dissolved in THF (160 mL) and Lawesson's reagent (6.9 g, 17.1 mmol) was added.
After 4 h the solvent was evaporated and the residue purified by flash-chromatography on silica gel (DCM-MeOH 95/5) affording 1.8 g (23%) of the title compound, crystallized from MeOH.
HPLC: R_t: 5.28 min
¹H NMR (600 MHz, DMSO-d₆) δ ppm 9.40 (br. s., 1H), 9.11 (br. s., 1H), 7.42-7.24 (m, 5H), 5.07 (s, 2H), 4.07 (d, J=13.2 Hz, 2H), 2.90-2.73 (m, 2H), 2.69 (tt, J=3.8, 11.6 Hz, 1H), 1.70-1.64 (m, 2H), 1.64-1.55 (m, 2H)
HRMS (ESI) [M+H]+ calcd for C₁₄H₁₈O₂N₂S 279.1162. found 279.1163.