Dichloromethane → HCID 66671763, compound

HRID 511192Notes

Reaction equation

HRID 511192 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]#[N:22])=[C:17]([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.[Cl:34]CCl>>[ClH:34].[NH:8]1[CH2:13][CH2:12][CH:11]([NH:14][C:15]2[CH:20]=[CH:19][C:18]([C:21]#[N:22])=[C:17]([C:23]([F:24])([F:25])[F:26])[CH:16]=2)[CH2:10][CH2:9]1

Participants

4

Reactant 3

HCID 6344DichloromethaneHCID 6422Trifluoroacetic acidHCID 58576648Tert-butyl 4-[[4-cyano-3-(trifluoromethyl)phenyl]amino]piperidine-1-carboxylate

Product 1

HCID 66671763HCID 66671763, compound

Procedure

To a solution of 4-(4-cyano-3-trifluoromethyl-phenylamino)-piperidine-1-carboxylic acid tert-butyl ester (250 mg; 0.68 mmol, prepared in accordance with Example 154) in dichloromethane (5 mL) is added trifluoroacetic acid (1.5 mL) and the reaction mixture is stirred at room temperature for 30 minutes. All volatiles are then removed under high vacuum and the residue is taken up with diethyl ether and concentrated again. The residue is dissolved in a minimum amount of dioxane and a 4 molar solution of hydrochloric acid in dioxane is added. The precipitate formed is collected, washed with diethyl ether and dried under high vacuum to afford the desired compound (225 mg; 0.74 mmol).

Workup

  1. customAll volatiles are then removed under high vacuum
  2. concentrationconcentrated again
  3. dissolutionThe residue is dissolved in a minimum amount of dioxane
  4. additiona 4 molar solution of hydrochloric acid in dioxane is added
  5. customThe precipitate formed
  6. customis collected
  7. washwashed with diethyl ether
  8. customdried under high vacuum

Sources & evidence

ORD record
ord-898df24aeb154ad9b1fbf2bf3834d0df
Source dataset
uspto-grants-2015_08
Patent number
US09096524B2

Reaction notes

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