1,4-Dioxane hydrochloride → HCID 68758453, compound

HRID 2382204Notes

Reaction equation

HRID 2382204 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([N:14]3[CH2:19][CH2:18][N:17](C(OC(C)(C)C)=O)[C@H:16]([CH3:27])[CH2:15]3)[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]2)=[CH:4][CH:3]=1.Cl.O1CCOCC1>O1CCOCC1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([N:14]3[CH2:19][CH2:18][NH:17][C@H:16]([CH3:27])[CH2:15]3)[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 204431481,4-Dioxane hydrochlorideHCID 68733962HCID 68733962, compound

Product 1

HCID 68758453HCID 68758453, compoundYield 84.1%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a solution of (R)-tert-butyl 4-(1-(4-chlorophenyl)cyclohexyl)-2-methylpiperazine-1-carboxylate (0.80 g, 2.03 mmol) in 1,4-dioxane (5 mL) at 0° C. was added dropwise a saturated solution dioxane-HCl (4 mL). The reaction mixture was warmed to room temperature and stirred for 2 h. The reaction mixture was concentrated under reduced pressure and the residue was washed with ethyl acetate. The pH of the residue was adjusted to 7 using aqueous 10% sodium carbonate solution and extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure to afford 0.5 g of (R)-1-(1-(4-chlorophenyl)cyclohexyl)-3-methylpiperazine.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. washthe residue was washed with ethyl acetate
  3. extractionextracted with ethyl acetate
  4. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-3af992a60d244c5996f1545e93914578
Source dataset
uspto-grants-2012_09
Patent number
US08258306B2

Reaction notes

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