Hydrochloric Acid → Hydrochloric Acid

HRID 511088Notes

Reaction equation

HRID 511088 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:24]3[CH:29]=[CH:28][C:27]([F:30])=[CH:26][CH:25]=3)(=[O:23])=[O:22])=[CH:17][CH:16]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.[ClH:31]>ClCCl.FC(F)(F)C(O)=O.C(OC(=O)C)C.O1CCOCC1>[ClH:31].[F:30][C:27]1[CH:26]=[CH:25][C:24]([S:21]([C:18]2[CH:19]=[CH:20][C:15]([NH:14][CH:11]3[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]3)=[CH:16][CH:17]=2)(=[O:23])=[O:22])=[CH:29][CH:28]=1.[ClH:31]

Participants

8

Reactant 2

HCID 313Hydrochloric AcidHCID 585762724-[4-(4-Fluoro-benzenesulfonyl)-phenylamino]-piperidine-1-carboxylic acid tert-butyl ester

Product 2

HCID 313Hydrochloric AcidHCID 66671912[4-(4-Fluoro-benzenesulfonyl)-phenyl]-piperidin-4-yl-amine hydrochloride

Reagents, catalysts & solvents 4

HCID 6344DichloromethaneSolvent2×HCID 6422Trifluoroacetic acidSolventHCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Procedure

4-[4-(4-Fluoro-benzenesulfonyl)-phenylamino]-piperidine-1-carboxylic acid tert-butyl ester (640 mg; 1.47 mmol, prepared in accordance with Example 31) is dissolved in a 1 to 1 mixture of dichloromethane and trifluoroacetic acid (2 mL) and the resulting solution is stirred at room temperature until complete conversion is observed (about 90 minutes). After concentration under reduced pressure, the residue obtained is co-evaporated with dichloromethane (2×10 mL). The crude residue is then diluted in ethylacetate (2 mL) and a 4N solution of hydrochloric acid in dioxane (3 mL) is added under stiffing. The solid formed is filtered and dried under high vacuum to afford the desired product as hydrochloride (546 mg; 1.47 mmol).

Workup

  1. custom(about 90 minutes)
  2. concentrationAfter concentration under reduced pressure
  3. customthe residue obtained
  4. customThe solid formed
  5. filtrationis filtered
  6. customdried under high vacuum

Sources & evidence

ORD record
ord-671b98c69c2a4a3cb7672fefe6574c42
Source dataset
uspto-grants-2015_08
Patent number
US09096524B2

Reaction notes

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