Dichloromethane → Hydrochloric Acid

HRID 511098Notes

Reaction equation

HRID 511098 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH:11]([NH:14][C:15]2[CH:20]=[CH:19][C:18]([S:21][C:22]([F:25])([F:24])[F:23])=[CH:17][CH:16]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.[Cl:26]CCl>FC(F)(F)C(O)=O>[ClH:26].[NH:8]1[CH2:13][CH2:12][CH:11]([NH:14][C:15]2[CH:16]=[CH:17][C:18]([S:21][C:22]([F:24])([F:23])[F:25])=[CH:19][CH:20]=2)[CH2:10][CH2:9]1.[ClH:26]

Participants

5

Reactant 2

HCID 6344DichloromethaneHCID 585766104-(4-Trifluoromethylsulfanyl-phenylamino)-piperidine-1-carboxylic acid tert-butyl ester

Product 2

HCID 313Hydrochloric AcidHCID 66671856Piperidin-4-yl-(4-trifluoromethylsulfanyl-phenyl)-amine hydrochloride

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

4-(4-Trifluoromethylsulfanyl-phenylamino)-piperidine-1-carboxylic acid tert-butyl ester (200 mg; 0.53 mmol, prepared in accordance with Example 46) is dissolved in a 1 to 1 mixture of dichloromethane and trifluoroacetic acid (2 mL), and stirred for 90 minutes. The mixture is concentrated under reduced pressure and co-evaporated with dichloromethane (2×10 mL). The resulting residue is diluted in ethylacetate (5 mL) and a 4N solution of hydrochloric acid in dioxane (5 mL) is added. A precipitate is obtained which is filtered and dried under high vacuum to afford the desired product as hydrochloride (168 mg; 0.53 mmol).

Workup

  1. concentrationThe mixture is concentrated under reduced pressure and co-evaporated with dichloromethane (2×10 mL)
  2. additionThe resulting residue is diluted in ethylacetate (5 mL)
  3. additiona 4N solution of hydrochloric acid in dioxane (5 mL) is added
  4. customA precipitate is obtained which
  5. filtrationis filtered
  6. customdried under high vacuum

Sources & evidence

ORD record
ord-f8318c9afbbb4998829cfc60b03c9519
Source dataset
uspto-grants-2015_08
Patent number
US09096524B2

Reaction notes

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