Potassium Carbonate → [3-(4-Chloro-phenyl)-allyl]-(3,4-difluoro-benzyl)-amine

HRID 597878Notes

Reaction equation

HRID 597878 reaction equation
C(OC(=O)[N:7]([CH2:17][CH:18]=[CH:19][C:20]1[CH:25]=[CH:24][C:23]([Cl:26])=[CH:22][CH:21]=1)[CH2:8][C:9]1[CH:14]=[CH:13][C:12]([F:15])=[C:11]([F:16])[CH:10]=1)(C)(C)C.C([O-])([O-])=O.[K+].[K+]>Cl.O1CCOCC1>[Cl:26][C:23]1[CH:22]=[CH:21][C:20]([CH:19]=[CH:18][CH2:17][NH:7][CH2:8][C:9]2[CH:14]=[CH:13][C:12]([F:15])=[C:11]([F:16])[CH:10]=2)=[CH:25][CH:24]=1

Participants

5

Reactant 2

HCID 11430Potassium CarbonateHCID 67271108[3-(4-Chloro-phenyl)-allyl]-(3,4-difluoro-benzyl)-carbamic acid tert-butyl ester

Product 1

HCID 67271292[3-(4-Chloro-phenyl)-allyl]-(3,4-difluoro-benzyl)-amineYield 97.9%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 312751,4-DioxaneSolvent

Procedure

A solution of [3-(4-chloro-phenyl)-allyl]-(3,4-difluoro-benzyl)-carbamic acid tert-butyl ester (2.04 g) in 20 mL of 4N HCl in dioxane was stirred at room temperature for 1 hr. The solution was poured into 150 mL of aq. K2CO3, and extracted with 3×50 mL of ethyl acetate. The combined organic layer was washed with 50 mL brine, dried over Na2SO4, filtered and concentrated to provide 1.49 g of [3-(4-chloro-phenyl)-allyl]-(3,4-difluoro-benzyl)-amine.

Workup

  1. extractionextracted with 3×50 mL of ethyl acetate
  2. washThe combined organic layer was washed with 50 mL brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-78dae3b997d646d796b8ecd46b25316a
Source dataset
uspto-grants-2011_03
Patent number
US07897601B2

Reaction notes

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