Trifluoroacetic acid → 4-(Piperidin-4-yl)aniline

HRID 1675126Notes

Reaction equation

HRID 1675126 reaction equation
C(O)(C(F)(F)F)=O.[NH2:8][C:9]1[CH:14]=[CH:13][C:12]([CH:15]2[CH2:20][CH2:19][N:18](C(OC(C)(C)C)=O)[CH2:17][CH2:16]2)=[CH:11][CH:10]=1>C(Cl)Cl>[NH:18]1[CH2:19][CH2:20][CH:15]([C:12]2[CH:13]=[CH:14][C:9]([NH2:8])=[CH:10][CH:11]=2)[CH2:16][CH2:17]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 21940085tert-Butyl 4-(4-aminophenyl)piperidine-1-carboxylate

Product 1

HCID 220478414-(Piperidin-4-yl)anilineYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

TFA (5 mL) was added to tert-butyl 4-(4-aminophenyl)piperidine-1-carboxylate (1.9 g, 6.87 mmol, CAS 170011-57-1) in DCM (5 mL). The resulting solution was stirred at ambient temperature for 2 hours then added to an SCX column. The desired product was eluted from the column using 2M ammonia in methanol and the solvent evaporated to dryness to give 4-(piperidin-4-yl)aniline (1.210 g, 100%) as a solid.

Workup

  1. additionthen added to an SCX column
  2. washThe desired product was eluted from the column
  3. customthe solvent evaporated to dryness

Sources & evidence

ORD record
ord-2112641b813048cf8f563501a85a5452
Source dataset
uspto-grants-2011_08
Patent number
US08003649B2

Reaction notes

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