Trifluoroacetic acid → 2-Nitro-4-(1-piperidin-4-ylmethoxy)5-methoxybenzonitrile

HRID 896252Notes

Reaction equation

HRID 896252 reaction equation
[N+:1]([C:4]1[CH:11]=[C:10]([O:12][CH2:13][CH:14]2[CH2:19][CH2:18][N:17](C(OC(C)(C)C)=O)[CH2:16][CH2:15]2)[C:9]([O:27][CH3:28])=[CH:8][C:5]=1[C:6]#[N:7])([O-:3])=[O:2].C(O)(C(F)(F)F)=O>C(Cl)Cl>[N+:1]([C:4]1[CH:11]=[C:10]([O:12][CH2:13][CH:14]2[CH2:15][CH2:16][NH:17][CH2:18][CH2:19]2)[C:9]([O:27][CH3:28])=[CH:8][C:5]=1[C:6]#[N:7])([O-:3])=[O:2]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 223496402-Nitro-4-((1-tert-butyloxycarbonylpiperidin-4-yl)methoxy)-5-methoxybenzonitrile

Product 1

HCID 223496252-Nitro-4-(1-piperidin-4-ylmethoxy)5-methoxybenzonitrileYield 88.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2-nitro-4-((1-tert-butyloxycarbonylpiperidin-4-yl)methoxy)-5-methoxybenzonitrile (1.17 g, 3 mmol) in CH2Cl2 (12 ml) was treated with TFA (2.4 ml) for 1 hour at room temperature. The solvent was evaporated, the residue was taken up in a mixture of CH2Cl2 and concentrated sodium bicarbonate, extracted with CH2Cl2. The organic phase was dried over MgSO4, concentrated to give title compound as a solid (770 mg, 88%).

Workup

  1. customThe solvent was evaporated
  2. additionthe residue was taken up in a mixture of CH2Cl2 and concentrated sodium bicarbonate
  3. extractionextracted with CH2Cl2
  4. dry with materialThe organic phase was dried over MgSO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-7da44072d0d249a1b6154bc0c03910f8
Source dataset
uspto-grants-2005_07
Patent number
US06919338B2

Reaction notes

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