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

HRID 883764

Reaction equation

HRID 883764 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-90cf636739a94777b71e82a1ef450b44
Source dataset
uspto-grants-2012_08
Patent number
US08236953B2

Linked notes

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