Trifluoroacetic acid → 3-[(Piperidin-4-yl)amino]benzonitrile

HRID 906343Notes

Reaction equation

HRID 906343 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([NH:9][CH:10]2[CH2:15][CH2:14][N:13](C(OC(C)(C)C)=O)[CH2:12][CH2:11]2)[CH:6]=[CH:7][CH:8]=1)#[N:2].C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH:13]1[CH2:12][CH2:11][CH:10]([NH:9][C:5]2[CH:4]=[C:3]([CH:8]=[CH:7][CH:6]=2)[C:1]#[N:2])[CH2:15][CH2:14]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 252237961,1-Dimethylethyl 4-[(3-cyanophenyl)amino]-1-piperidinecarboxylate

Product 1

HCID 252237973-[(Piperidin-4-yl)amino]benzonitrileYield 125.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 1,1-dimethylethyl 4-[(3-cyanophenyl)amino]-1-piperidinecarboxylate (D5) (750 mg, 2.43 mmol) in DCM (30 ml) was cooled in an ice bath and TFA (6 ml) was added. The reaction mixture was then stirred at room temperature for 1 h. The solvent was removed in vacuo and the residue loaded onto an Isolute SCX cartridge. Elution with MeOH (100 ml) followed by 2M NH3 in MeOH (100 ml) gave the title compound as a white solid (613 mg). δH (CDCl3, 250 MHz) 7.21 (2H, t), 6.93 (1H, m), 6.77 (2H, m), 3.78 (1H, m), 3.35 (1H, m), 3.14 (2H, m), 2.73 (2H, m), 2.06 (2H, m), 1.34 (2H, m). MS (ES): MH+ 202.

Workup

  1. customThe solvent was removed in vacuo
  2. washElution with MeOH (100 ml)

Sources & evidence

ORD record
ord-ef7be570f2614b3cbbe9b3668ffb6bb8
Source dataset
uspto-grants-2011_09
Patent number
US08012981B2

Reaction notes

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