Trifluoroacetic acid → Hydrochloric Acid

HRID 511077Notes

Reaction equation

HRID 511077 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH:11]([NH:14][C:15]2[CH:20]=[CH:19][C:18]([Cl:21])=[C:17]([S:22][C:23]([F:26])([F:25])[F:24])[CH:16]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.FC(F)(F)C(O)=O>ClCCl>[ClH:21].[Cl:21][C:18]1[CH:19]=[CH:20][C:15]([NH:14][CH:11]2[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]2)=[CH:16][C:17]=1[S:22][C:23]([F:26])([F:24])[F:25].[ClH:21]

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acidHCID 585760114-(4-Chloro-3-trifluoromethylsulfanyl-phenylamino)-piperidine-1-carboxylic acid tert-butyl ester

Product 2

HCID 313Hydrochloric AcidYield 297.9%HCID 66671939(4-Chloro-3-trifluoromethylsulfanyl-phenyl)-piperidin-4-yl-amine hydrochloride

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4-(4-Chloro-3-trifluoromethylsulfanyl-phenylamino)-piperidine-1-carboxylic acid tert-butyl ester (580 mg; 1.41 mmol, prepared in accordance with Example 15) is dissolved in dichloromethane (8 mL) and trifluoroacetic acid (2 mL) is slowly added under stirring. After 60 minutes reaction time, the mixture is concentrated under reduced pressure and co-evaporated twice with dichloromethane (10 mL). The crude residue is then diluted in dioxane (2 mL) and a 4N solution of hydrochloric acid in dioxane (3 mL) is added under stirring. A solid is formed which is then filtered and dried under high vacuum to afford the desired product as hydrochloride (484 mg; 1.40 mmol).

Workup

  1. customAfter 60 minutes reaction time
  2. concentrationthe mixture is concentrated under reduced pressure
  3. additionThe crude residue is then diluted in dioxane (2 mL)
  4. additiona 4N solution of hydrochloric acid in dioxane (3 mL) is added
  5. stirringunder stirring
  6. customA solid is formed which
  7. filtrationis then filtered
  8. customdried under high vacuum

Sources & evidence

ORD record
ord-856a9e958f3b43ee933f727793558060
Source dataset
uspto-grants-2015_08
Patent number
US09096524B2

Reaction notes

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