Piperidine → (R)-2-(4-propyl-benzylcarbamoyl)-4-thiocarbamoyl-piperazine-1-carboxylic acid benzyl ester

HRID 908598Notes

Reaction equation

HRID 908598 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][NH:14][CH2:13][C@@H:12]1[C:17](=[O:29])[NH:18][CH2:19][C:20]1[CH:25]=[CH:24][C:23]([CH2:26][CH2:27][CH3:28])=[CH:22][CH:21]=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.C1C2C(COC([N:54]=[C:55]=[S:56])=O)C3C(=CC=CC=3)C=2C=CC=1.N1CCCCC1>C(Cl)(Cl)Cl>[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][N:14]([C:55](=[S:56])[NH2:54])[CH2:13][C@@H:12]1[C:17](=[O:29])[NH:18][CH2:19][C:20]1[CH:25]=[CH:24][C:23]([CH2:26][CH2:27][CH3:28])=[CH:22][CH:21]=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 8082PiperidineHCID 8471TriethylamineHCID 4154759Fmoc isothiocyanateHCID 59703714(R)-2-(4-propyl-benzylcarbamoyl)-piperazine-1-carboxylic acid benzyl ester

Product 1

HCID 59703710(R)-2-(4-propyl-benzylcarbamoyl)-4-thiocarbamoyl-piperazine-1-carboxylic acid benzyl esterYield 88.7%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a solution of the compound (1.59 g) obtained in Step 3 in chloroform (16 ml) was added, with stirring at room temperature, triethylamine (840 μl), and 9-fluorenylmethoxycarbonyl isothiocyanate (1.13 g) was added. After stirring at room temperature for 4 hr, piperidine (805 μl) was added. After stirring overnight at room temperature, the reaction mixture was concentrated under reduced pressure. The residue was partitioned by adding ethyl acetate and water. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, filtrated, and concentrated under reduced pressure. The residue was purified by column chromatography (ethyl acetate:n-hexane=1:1-4:1) to give the title compound (1.62 g).

Workup

  1. stirringAfter stirring at room temperature for 4 hr
  2. stirringAfter stirring overnight at room temperature
  3. concentrationthe reaction mixture was concentrated under reduced pressure
  4. customThe residue was partitioned
  5. additionby adding ethyl acetate and water
  6. washThe organic layer was washed with saturated brine
  7. dry with materialdried over anhydrous magnesium sulfate
  8. filtrationfiltrated
  9. concentrationconcentrated under reduced pressure
  10. customThe residue was purified by column chromatography (ethyl acetate:n-hexane=1:1-4:1)

Sources & evidence

ORD record
ord-233ef38926434d7685e3c80b848a1f03
Source dataset
uspto-grants-2011_09
Patent number
US08017612B2

Reaction notes

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