Trifluoroacetic acid → 1-(4-Methoxybenzyl)piperidin-4-amine

HRID 745841Notes

Reaction equation

HRID 745841 reaction equation
CC([N:5]([CH:9]1[CH2:14][CH2:13][N:12]([CH2:15][C:16]2[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][CH:17]=2)[CH2:11][CH2:10]1)C(=O)[O-])(C)C.FC(F)(F)C(O)=O>C(Cl)Cl>[NH2:5][CH:9]1[CH2:10][CH2:11][N:12]([CH2:15][C:16]2[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][CH:17]=2)[CH2:13][CH2:14]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acid2×HCID 867409101,1-Dimethylethyl1-[(4-methoxyphenyl)methyl]-4-piperidinylcarbamate

Product 1

HCID 126418411-(4-Methoxybenzyl)piperidin-4-amine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 1,1-dimethylethyl1-[(4-methoxyphenyl)methyl]-4-piperidinylcarbamate (0.02 mole) and trifluoroacetic acid (0.01 mole) in 50 ml. of methylene chloride was refluxed for a 3 hr. period. Additional trifluoroacetic acid (0.08 mole) was added and reflux continued for an additional 30 minutes. The crude solution was evaporated in vacuo, residual material dissolved in water and the aqueous phase washed with ether and then made basic with 50% sodium hydroxide. Extraction of the basified solution with chloroform, drying of the chloroform extracts, and removal of the solvent afforded 4-amino-1-[(4-methoxyphenyl)methyl]piperidine in nearly quantitative yield.

Workup

  1. temperaturereflux
  2. customThe crude solution was evaporated in vacuo, residual material
  3. dissolutiondissolved in water
  4. washthe aqueous phase washed with ether
  5. extractionExtraction of the basified solution with chloroform
  6. dry with materialdrying of the chloroform
  7. customremoval of the solvent

Sources & evidence

ORD record
ord-c9b584e53eda48e380c86daee098c7b2
Source dataset
uspto-grants-1986_07
Patent number
US04600758

Reaction notes

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