Trifluoroacetic acid → 2-Fluoro-4-(piperidin-4-ylmethyl)aniline

HRID 515290Notes

Reaction equation

HRID 515290 reaction equation
[NH2:1][C:2]1[CH:21]=[CH:20][C:5]([CH2:6][CH:7]2[CH2:12][CH2:11][N:10](C(OC(C)(C)C)=O)[CH2:9][CH2:8]2)=[CH:4][C:3]=1[F:22].FC(F)(F)C(O)=O>ClCCl>[F:22][C:3]1[CH:4]=[C:5]([CH2:6][CH:7]2[CH2:8][CH2:9][NH:10][CH2:11][CH2:12]2)[CH:20]=[CH:21][C:2]=1[NH2:1]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 67193052Tert-butyl 4-(4-amino-3-fluorobenzyl)piperidine-1-carboxylate

Product 1

HCID 671959362-Fluoro-4-(piperidin-4-ylmethyl)anilineYield 118.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Tert-butyl 4-(4-amino-3-fluorobenzyl)piperidine-1-carboxylate (6.49 mmol, 2 g) was dissolved in dichloromethane (5 mL). Trifluoroacetic acid (3 mL) was added and the reaction mixture stirred at room temperature for 30 minutes. The reaction mixture was purified by SCX chromatography to give the intermediate 2-fluoro-4-(piperidin-4-ylmethyl)aniline (1.6 g) as a colourless oil.

Workup

  1. customThe reaction mixture was purified by SCX chromatography

Sources & evidence

ORD record
ord-76db2c94a0b54794bb75234748a516d8
Source dataset
uspto-grants-2015_08
Patent number
US09108939B2

Reaction notes

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