HCID 19363748, compound → HCID 85981203, compound

HRID 2245303Notes

Reaction equation

HRID 2245303 reaction equation
[F:1][C:2]([F:28])([F:27])[C:3]1[CH:8]=[CH:7][C:6]([C:9]([C:17]2[CH:22]=[CH:21][C:20]([C:23]([F:26])([F:25])[F:24])=[CH:19][CH:18]=2)(O)[CH:10]2[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]2)=[CH:5][CH:4]=1>FC(F)(F)C(O)=O>[F:26][C:23]([F:24])([F:25])[C:20]1[CH:19]=[CH:18][C:17]([C:9]([C:6]2[CH:7]=[CH:8][C:3]([C:2]([F:28])([F:1])[F:27])=[CH:4][CH:5]=2)=[C:10]2[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]2)=[CH:22][CH:21]=1

Participants

3

Reactant 1

HCID 19363748HCID 19363748, compound

Product 1

HCID 85981203HCID 85981203, compoundYield 94.5%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of 10.0 grams (0.025 mole) of 4-{bis[4-(trifluoromethyl)phenyl]hydroxymethyl}piperidine (known compound) in 50 mL of trifluoroacetic acid was heated to 70° C. where it stirred for four hours. After this time, excess trifluoroacetic acid was removed by distillation. The residue remaining from the distillation was added drop wise to ice water. Upon completion of addition, the mixture was neutralized with an aqueous solution saturated with potassium carbonate. The mixture was then extracted with methylene chloride, and the extract was washed with an aqueous solution saturated with sodium chloride. The extract was concentrated under reduced pressure to a residue, and the residue was crystallized in hexane, yielding in two crops, 9.1 grams of the subject compound. The NMR spectrum was consistent with the proposed structure.

Workup

  1. customAfter this time, excess trifluoroacetic acid was removed by distillation
  2. distillationThe residue remaining from the distillation
  3. additionwas added drop wise to ice water
  4. additionUpon completion of addition
  5. extractionThe mixture was then extracted with methylene chloride
  6. washthe extract was washed with an aqueous solution saturated with sodium chloride
  7. concentrationThe extract was concentrated under reduced pressure to a residue
  8. customthe residue was crystallized in hexane

Sources & evidence

ORD record
ord-dcdeb35d17bd48b7b29c7a2bdc3829d2
Source dataset
uspto-grants-2010_03
Patent number
US07683070B2

Reaction notes

Loading…