1,4-Dioxane hydrochloride → (R)-2-(4-propyl-benzylcarbamoyl)-piperazine-1-carboxylic acid benzyl ester

HRID 908597Notes

Reaction equation

HRID 908597 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][N:11]([C:14]([O:16][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[O:15])[C@@H:10]([C:24](=[O:36])[NH:25][CH2:26][C:27]2[CH:32]=[CH:31][C:30]([CH2:33][CH2:34][CH3:35])=[CH:29][CH:28]=2)[CH2:9]1)=O)(C)(C)C.Cl.O1CCOCC1>O1CCOCC1>[CH2:17]([O:16][C:14]([N:11]1[CH2:12][CH2:13][NH:8][CH2:9][C@@H:10]1[C:24](=[O:36])[NH:25][CH2:26][C:27]1[CH:32]=[CH:31][C:30]([CH2:33][CH2:34][CH3:35])=[CH:29][CH:28]=1)=[O:15])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

4

Reactant 2

HCID 204431481,4-Dioxane hydrochlorideHCID 59703767(R)-2-(4-propyl-benzylcarbamoyl)-piperazine-1,4-dicarboxylic acid 1-benzyl ester 4-tert-butyl ester

Product 1

HCID 59703714(R)-2-(4-propyl-benzylcarbamoyl)-piperazine-1-carboxylic acid benzyl esterYield 75.5%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To the compound (2.64 g) obtained in Step 2 in 1,4-dioxane (13 ml) was added, with stirring at room temperature, 4N hydrogen chloride/1,4-dioxane (13 ml). After stirring at room temperature for 3 hr, the reaction mixture was concentrated under reduced pressure. Toluene was added to the residue, and the mixture was concentrated again under reduced pressure. The residue was partitioned by adding ethyl acetate and saturated aqueous sodium hydrogen carbonate solution. The organic layer was washed successively with water and saturated brine, dried over anhydrous magnesium sulfate, filtrated, and concentrated under reduced pressure. The residue was purified by column chromatography (5%-10% methanol/chloroform) to give the title compound (1.59 g).

Workup

  1. stirringAfter stirring at room temperature for 3 hr
  2. concentrationthe reaction mixture was concentrated under reduced pressure
  3. additionToluene was added to the residue
  4. concentrationthe mixture was concentrated again under reduced pressure
  5. customThe residue was partitioned
  6. additionby adding ethyl acetate and saturated aqueous sodium hydrogen carbonate solution
  7. washThe organic layer was washed successively with water and saturated brine
  8. dry with materialdried over anhydrous magnesium sulfate
  9. filtrationfiltrated
  10. concentrationconcentrated under reduced pressure
  11. customThe residue was purified by column chromatography (5%-10% methanol/chloroform)

Sources & evidence

ORD record
ord-d86a43cfabe74a408b8e4a9257070d1d
Source dataset
uspto-grants-2011_09
Patent number
US08017612B2

Reaction notes

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