benzyl 4-[amino(thiocarbonyl)]piperidine-1-carboxylate synthesis
- Product Name:benzyl 4-[amino(thiocarbonyl)]piperidine-1-carboxylate
- CAS Number:167757-46-2
- Molecular formula:C14H18N2O2S
- Molecular Weight:278.37
167757-45-1
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$22.00/1g
167757-46-2
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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: Rt: 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.
References:
US2013/324551,2013,A1 Location in patent:Paragraph 0318; 0319; 0320; 0321
19172-47-5
303 suppliers
$9.00/1g
167757-45-1
97 suppliers
$22.00/1g
167757-46-2
24 suppliers
$187.33/1gm:
39546-32-2
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$6.00/5g
167757-46-2
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$187.33/1gm:
501-53-1
409 suppliers
$10.00/1g
167757-46-2
24 suppliers
$187.33/1gm:
39546-32-2
361 suppliers
$6.00/5g
501-53-1
409 suppliers
$10.00/1g
167757-46-2
24 suppliers
$187.33/1gm: