Trifluoroacetic acid → HCID 53864130, compound

HRID 1079389Notes

Reaction equation

HRID 1079389 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][O:15][C:16]2[CH:21]=[CH:20][C:19]([N:22]([CH3:24])[CH3:23])=[CH:18][CH:17]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.FC(F)(F)C(O)=O>>[CH3:23][N:22]([CH3:24])[C:19]1[CH:18]=[CH:17][C:16]([O:15][CH2:14][CH:11]2[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]2)=[CH:21][CH:20]=1

Participants

3

Reactant 2

HCID 6422Trifluoroacetic acidHCID 23366953HCID 23366953, compound

Product 1

HCID 53864130HCID 53864130, compoundYield 142.7%

Procedure

To 1-tert-Butyloxycarbonyl-4-[(4-dimethylaminophenyloxy)methyl]piperidine (0.1 g) obtained in Example 13 was added trifluoroacetic acid (0.5 ml) followed by stirring at room temperature for 10 minutes. The reaction mixture was concentrated under reduced pressure, and the concentrate was diluted with methylene chloride (100 ml) and washed with aqueous saturated solution of sodium bicarbonate. The organic layer was separated, dried over sodium sulfate and concentrated under reduced pressure. The residue was treated with fumaric acid and the resulting fumarate was recrystallized from methanol to obtain 4-[(4-dimethylaminophenyloxy)methyl]piperidine 1/2 fumarate (0.1 g) as pale yellow crystals, m.p. 210°-213° C.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. additionthe concentrate was diluted with methylene chloride (100 ml)
  3. washwashed with aqueous saturated solution of sodium bicarbonate
  4. customThe organic layer was separated
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. additionThe residue was treated with fumaric acid
  8. customthe resulting fumarate was recrystallized from methanol

Sources & evidence

ORD record
ord-b35a066468e2454eae31ef296f8b4c30
Source dataset
uspto-grants-1996_12
Patent number
US05580883

Reaction notes

Loading…