Trifluoroacetic acid → 3-Aminopropyl-4-methyl-4-phenylpiperidine

HRID 2085425Notes

Reaction equation

HRID 2085425 reaction equation
FC(F)(F)C(O)=O.C(OC([NH:15][CH2:16][CH2:17][CH2:18][N:19]1[CH2:24][CH2:23][C:22]([CH3:31])([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH2:21][CH2:20]1)O)(C)(C)C>ClCCl>[CH3:31][C:22]1([C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=2)[CH2:21][CH2:20][N:19]([CH2:18][CH2:17][CH2:16][NH2:15])[CH2:24][CH2:23]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 69866729HCID 69866729, compound

Product 1

HCID 107996093-Aminopropyl-4-methyl-4-phenylpiperidineYield 98%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trifluoroacetic acid (1 mL) was added to tert-butoxy{[3-(4-methyl-4-phenyl-1-piperdinyl)propyl]-amino}methanol (0.500 g, 1.51 mmol) in dichloromethane (5 mL) and the solution was stirred at room temperature for 1 h. The solution was concentrated, neutralized with 10% KOH solution and extracted with dichloromethane (25 mL). The organic layer was dried over sodium sulfate, filtered and concentrated, giving 0.340 g (98%) of 3-(4-methyl-4-phenyl-1-piperdinyl)propylamine which was used without further purification in the subsequent step.

Workup

  1. concentrationThe solution was concentrated
  2. extractionextracted with dichloromethane (25 mL)
  3. dry with materialThe organic layer was dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-7af854a8c01444d3bacee39893894ccc
Source dataset
uspto-grants-2004_04
Patent number
US06720324B2

Reaction notes

Loading…