Hydrochloric Acid → (2-(3-Chloro-4-fluorophenyl)-6-(trifluoromethyl)pyridin-3-yl)methanamine hydrochloride

HRID 1428720Notes

Reaction equation

HRID 1428720 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2[C:14]([CH2:15][NH:16]C(=O)OC(C)(C)C)=[CH:13][CH:12]=[C:11]([C:24]([F:27])([F:26])[F:25])[N:10]=2)[CH:5]=[CH:6][C:7]=1[F:8].Cl>O1CCOCC1>[ClH:1].[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2[C:14]([CH2:15][NH2:16])=[CH:13][CH:12]=[C:11]([C:24]([F:26])([F:27])[F:25])[N:10]=2)[CH:5]=[CH:6][C:7]=1[F:8]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 86676126Tert-butyl (2-(3-chloro-4-fluorophenyl)-6-(trifluoromethyl)pyridin-3-yl)methylcarbamate

Product 1

HCID 86676125(2-(3-Chloro-4-fluorophenyl)-6-(trifluoromethyl)pyridin-3-yl)methanamine hydrochlorideYield 186.1%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

To a stirred solution of tert-butyl (2-(3-chloro-4-fluorophenyl)-6-(trifluoromethyl)pyridin-3-yl)methylcarbamate (5.27 g, 13.04 mmol) in 1,4-dioxane (5 mL) was added with 1,4-dioxane.HCl (10 mL) under cooling and the reaction mixture was allowed to stir for 12 h. The reaction mixture was concentrated under reduced pressure and was co-distilled with methanol thrice and the solid obtained was filtered through sintered funnel and was washed with 10% ethyl acetate in n-hexane to afford pure (2-(3-chloro-4-fluorophenyl)-6-(trifluoromethyl)pyridin-3-yl)methanamine hydrochloride (4.14 g, 93%).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customthe solid obtained
  3. filtrationwas filtered through sintered funnel
  4. washwas washed with 10% ethyl acetate in n-hexane

Sources & evidence

ORD record
ord-5cb278c6377745b4902d16be65da6410
Source dataset
uspto-grants-2015_01
Patent number
US08937092B2

Reaction notes

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