Trifluoroacetic acid → HCID 67748307, compound

HRID 1079409Notes

Reaction equation

HRID 1079409 reaction equation
FC(F)(F)C(O)=O.C(OC([N:15]1[CH2:20][CH2:19][CH:18]([O:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=2[N:28]([C:35](=[O:37])[CH3:36])[CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH3:34])[CH2:17][CH2:16]1)=O)(C)(C)C>>[C:35]([N:28]([C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][C:22]=1[O:21][CH:18]1[CH2:19][CH2:20][NH:15][CH2:16][CH2:17]1)[CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH3:34])(=[O:37])[CH3:36]

Participants

3

Reactant 2

HCID 6422Trifluoroacetic acidHCID 67748269HCID 67748269, compound

Product 1

HCID 67748307HCID 67748307, compoundYield 102%

Procedure

Trifluoroacetic acid (25 ml) was added to 1-tert-butyloxycarbonyl-4-(N-acetyl-N-hexylaminophenyloxy)piperidine (12.5 g) with ice-cooling and the mixture was stirred at room temperature for 1 hour. The reaction mixture was concentrated and methylene chloride (50 ml) was added to the residue and the mixture was washed with aqueous saturated solution of sodium bicarbonate. The aqueous layer was extracted with methylene chloride (50 ml×3), the combined organic layer were dried over anhydrous sodium sulfate and the solvent was distilled off to obtain 4-(N-acetyl-N-hexylaminophenyloxy)piperidine (9.7 g) as a brown oil.

Workup

  1. temperaturecooling
  2. concentrationThe reaction mixture was concentrated
  3. additionmethylene chloride (50 ml) was added to the residue
  4. washthe mixture was washed with aqueous saturated solution of sodium bicarbonate
  5. extractionThe aqueous layer was extracted with methylene chloride (50 ml×3)
  6. dry with materialthe combined organic layer were dried over anhydrous sodium sulfate
  7. distillationthe solvent was distilled off

Sources & evidence

ORD record
ord-7c13e4957769429f9bc8186a5fdfd03d
Source dataset
uspto-grants-1996_12
Patent number
US05580883

Reaction notes

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