Hydrochloric Acid → 1-(3,5-Difluoropyridin-2-yl)ethan-1-amine

HRID 1641413Notes

Reaction equation

HRID 1641413 reaction equation
C(OC(=O)[NH:7][CH:8]([C:10]1[C:15]([F:16])=[CH:14][C:13]([F:17])=[CH:12][N:11]=1)[CH3:9])(C)(C)C.Cl>C(Cl)Cl.O1CCOCC1>[F:16][C:15]1[C:10]([CH:8]([NH2:7])[CH3:9])=[N:11][CH:12]=[C:13]([F:17])[CH:14]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 129968424tert-Butyl-1-(3,5-difluoropyridin-2-yl)ethylcarbamate

Product 1

HCID 583673901-(3,5-Difluoropyridin-2-yl)ethan-1-amineYield 97.3%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent

Procedure

To tert-butyl-1-(3,5-difluoropyridin-2-yl)ethylcarbamate (Method 16; 0.10 g, 0.39 mmol) in DCM (2 ml) was added HCl (0.8 ml, 3.12 mmol) in dioxane. The reaction was stirred at room temperature for 3 hours. The solvent was removed and 10 ml of saturated sodium bicarbonate was added. The resulting aqueous solution was extracted with ether (5×30 ml), dried over sodium sulfate and concentrated to give the title compound (0.06 g, 95%) as pale yellow oil. MS: Calcd.: 158. Found: [M+H]+ 159.

Workup

  1. customThe solvent was removed
  2. addition10 ml of saturated sodium bicarbonate was added
  3. extractionThe resulting aqueous solution was extracted with ether (5×30 ml)
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-2aed46d78b8d4ca68e99ddc4d6c933eb
Source dataset
uspto-grants-2012_02
Patent number
US08114989B2

Reaction notes

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