Hydrochloric Acid → HCID 67376533, compound

HRID 1023346Notes

Reaction equation

HRID 1023346 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([CH2:8][CH2:9][O:10][C:11]2[CH:16]=[CH:15][C:14]([C:17]([F:20])([F:19])[F:18])=[CH:13][CH:12]=2)[CH:5]=[CH:4][C:3]=1[CH:21]1OCCO1.Cl.[N:27]1([C:33]([O:35][C:36]([CH3:39])([CH3:38])[CH3:37])=[O:34])[CH2:32][CH2:31][NH:30][CH2:29][CH2:28]1.C([O-])(O)=O.[Na+]>C(Cl)Cl.C1COCC1>[F:1][C:2]1[CH:7]=[C:6]([CH2:8][CH2:9][O:10][C:11]2[CH:16]=[CH:15][C:14]([C:17]([F:18])([F:19])[F:20])=[CH:13][CH:12]=2)[CH:5]=[CH:4][C:3]=1[CH2:21][N:30]1[CH2:31][CH2:32][N:27]([C:33]([O:35][C:36]([CH3:39])([CH3:38])[CH3:37])=[O:34])[CH2:28][CH2:29]1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 143452tert-Butyl piperazine-1-carboxylateHCID 516892Sodium BicarbonateHCID 67327154HCID 67327154, compound

Product 1

HCID 67376533HCID 67376533, compoundYield 68.4%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a THF (10 mL) solution of 2-(2-fluoro-4-{2-[4-(trifluoromethyl)phenoxy]-ethyl}phenyl)-1,3-dioxolane (0.552 g) was added 6 M HCl (0.775 mL) at 0° C., then the resultant mixture was room temperature for 5 hours. The reaction mixture was evaporated to afford a pale yellow oil. To a CH2Cl2 (15 mL) solution of that pale yellow oil and tert-Butyl 1-piperazinecarboxylate (0.375 g) were added NaB(OAc)3 (0.657 g) at 0° C. The resultant mixture was stirred at room temperature for 3 days. To the reaction mixture was added saturated aqueous NaHCO3, and extracted with CH2Cl2. The organic layer was washed with saturated aqueous NaCl, dried over anhydrous MgSO4, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (n-hexane/AcOEt=9/1 to 4/1) to afford tert-butyl 4-(2-fluoro-4-{2-[4-(trifluoromethyl)phenoxy]ethyl}benzyl)piperazine-1-carboxylate as a colorless oil (0.511 g).

Workup

  1. customThe reaction mixture was evaporated
  2. customto afford a pale yellow oil
  3. extractionextracted with CH2Cl2
  4. washThe organic layer was washed with saturated aqueous NaCl
  5. dry with materialdried over anhydrous MgSO4
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (n-hexane/AcOEt=9/1 to 4/1)

Sources & evidence

ORD record
ord-3141362291394f5b9fc925dc89a6a8be
Source dataset
uspto-grants-2014_05
Patent number
US08722663B2

Reaction notes

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