Hydrochloric Acid → HCID 42634360, compound

HRID 2262504Notes

Reaction equation

HRID 2262504 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][O:11][CH2:10][C@@H:9]1[CH2:14][O:15][C:16]([N:18]1[CH2:23][CH2:22][N:21]([C:24]2[CH:29]=[CH:28][C:27]([F:30])=[CH:26][CH:25]=2)[CH2:20][CH2:19]1)=[O:17])=O)(C)(C)C.Cl>O1CCOCC1>[F:30][C:27]1[CH:28]=[CH:29][C:24]([N:21]2[CH2:20][CH2:19][N:18]([C:16]([O:15][CH2:14][C@H:9]3[CH2:10][O:11][CH2:12][CH2:13][NH:8]3)=[O:17])[CH2:23][CH2:22]2)=[CH:25][CH:26]=1

Participants

4

Reactant 2

HCID 313Hydrochloric Acid2×HCID 66934484HCID 66934484, compound

Product 1

HCID 42634360HCID 42634360, compoundYield 99.7%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent3×

Procedure

(3R)-3-[4-(4-Fluorophenyl)-piperazine-1-carbonyloxymethyl]-morpholine-4-carboxylic acid tert-butyl ester (5.07 g, 12.0 mmol) was stirred in dry dioxane (35 mL) at room temperature and HCl in dioxane (4M; 15 mL, 60 mmol) was added dropwise. The reaction mixture was stirred for 24 h at room temperature. A further portion of HCl in dioxane (4M; 10 mL, 40 mmol) was added and stirred overnight. The dioxane was decanted and the residual gum was washed with dioxane (×3) and Et2O (×2). The residue was partitioned between DCM (300 mL) and 1.2M aqueous NaHCO3. The aqueous layer was extracted with DCM (2×200 mL). The combined DCM extracts were dried (Na2SO4) and the solvent removed in vacuo. The residue was dissolved in DCM and dried in vacuo to give (3R)-morpholin-3-ylmethyl 4-(4-fluorophenyl)piperazine-1-carboxylate (3.87 g, quant.) as an off white solid.

Workup

  1. stirringstirred overnight
  2. customThe dioxane was decanted
  3. washthe residual gum was washed with dioxane (×3) and Et2O (×2)
  4. customThe residue was partitioned between DCM (300 mL) and 1.2M aqueous NaHCO3
  5. extractionThe aqueous layer was extracted with DCM (2×200 mL)
  6. dry with materialThe combined DCM extracts were dried (Na2SO4)
  7. customthe solvent removed in vacuo
  8. dissolutionThe residue was dissolved in DCM
  9. customdried in vacuo

Sources & evidence

ORD record
ord-189d86d917804d1cbd52e25ea7f50ffd
Source dataset
uspto-grants-2010_12
Patent number
US07851471B2

Reaction notes

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