Hydrochloric Acid → Hydrochloric Acid

HRID 511101Notes

Reaction equation

HRID 511101 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH:11]([NH:14][C:15]2[CH:20]=[CH:19][C:18]([C:21]([F:24])([F:23])[F:22])=[CH:17][N:16]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.FC(F)(F)C(O)=O.[ClH:32]>ClCCl.O1CCOCC1>[ClH:32].[NH:8]1[CH2:9][CH2:10][CH:11]([NH:14][C:15]2[CH:20]=[CH:19][C:18]([C:21]([F:23])([F:22])[F:24])=[CH:17][N:16]=2)[CH2:12][CH2:13]1.[ClH:32]

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 6422Trifluoroacetic acidHCID 58576452HCID 58576452, compound

Product 2

HCID 313Hydrochloric AcidHCID 66671897HCID 66671897, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 312751,4-DioxaneSolvent2×

Procedure

4-(5-Trifluoromethyl-pyridin-2-ylamino)-piperidine-1-carboxylic acid tert-butyl ester (460 mg; 1.33 mmol, prepared in accordance with Example 49) is dissolved in dichloromethane (6 mL) and trifluoroacetic acid (1 mL) is added under stirring. After 30 minutes reaction time, the solution is concentrated under reduced pressure and the residue obtained is co-evaporated with dichloromethane (5 mL). The product isolated is dissolved in dioxane (2 mL) and a 4N solution of hydrochloric acid in dioxane (3 mL) is added. The precipitate formed is filtered, rapidly rinsed with a small amount of dioxane and is dried under high vacuum to afford the desired product as hydrochloride (352 mg; 1.25 mmol).

Workup

  1. customAfter 30 minutes reaction time
  2. concentrationthe solution is concentrated under reduced pressure
  3. customthe residue obtained
  4. customThe product isolated
  5. customThe precipitate formed
  6. filtrationis filtered
  7. washrapidly rinsed with a small amount of dioxane
  8. customis dried under high vacuum

Sources & evidence

ORD record
ord-9b560bd1b096498e8b4185e815ea1143
Source dataset
uspto-grants-2015_08
Patent number
US09096524B2

Reaction notes

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