Dichloromethane → Hydrochloric Acid

HRID 511104Notes

Reaction equation

HRID 511104 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH:11]([NH:14][C:15]2[CH:20]=[CH:19][C:18]([O: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]([O:21][C:22]([F:23])([F:24])[F:25])=[CH:19][CH:20]=2)[CH2:10][CH2:9]1.[ClH:26]

Participants

5

Reactant 2

HCID 6344DichloromethaneHCID 66237091-(Tert-butoxycarbonyl)-4-[[4-(trifluoromethoxy)phenyl]amino]piperidine

Product 2

HCID 313Hydrochloric AcidHCID 66678709Piperidin-4-yl-(4-trifluoromethoxy-phenyl)-amine hydrochloride

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

4-(4-Trifluoromethoxy-phenylamino)-piperidine-1-carboxylic acid tert-butyl ester (380 mg; 1.06 mmol, prepared in accordance with Example 52) 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 (275 mg; 0.93 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-6849f471ce6a42ffae0800609153183c
Source dataset
uspto-grants-2015_08
Patent number
US09096524B2

Reaction notes

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