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

HRID 2412937Notes

Reaction equation

HRID 2412937 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][N:10]2[CH2:15][CH2:14][CH:13]([NH:16]C(=O)OC(C)(C)C)[CH2:12][CH2:11]2)=[CH:5][CH:4]=1.FC(F)(F)C(O)=O>C(Cl)Cl>[NH2:16][CH:13]1[CH2:12][CH2:11][N:10]([CH2:9][C:6]2[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=2)[CH2:15][CH2:14]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acid2×HCID 13370621tert-Butyl 1-(4-methoxybenzyl)piperidin-4-ylcarbamate

Product 1

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

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 1,1-dimethylethyl 1-[(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-95a4e2ac6e484fb2988ddcb7bf3474b4
Source dataset
uspto-grants-1985_01
Patent number
US04495194

Reaction notes

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