Trifluoroacetic acid → 4-{2-[(Piperidin-4-yl)oxy]pyrimidin-5-yl}benzonitrile

HRID 1666540Notes

Reaction equation

HRID 1666540 reaction equation
FC(F)(F)C(O)=O.C(OC([N:15]1[CH2:20][CH2:19][CH:18]([O:21][C:22]2[N:27]=[CH:26][C:25]([C:28]3[CH:33]=[CH:32][C:31]([C:34]#[N:35])=[CH:30][CH:29]=3)=[CH:24][N:23]=2)[CH2:17][CH2:16]1)=O)(C)(C)C>C(Cl)Cl>[NH:15]1[CH2:16][CH2:17][CH:18]([O:21][C:22]2[N:23]=[CH:24][C:25]([C:28]3[CH:33]=[CH:32][C:31]([C:34]#[N:35])=[CH:30][CH:29]=3)=[CH:26][N:27]=2)[CH2:19][CH2:20]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 23115990HCID 23115990, compound

Product 1

HCID 231159714-{2-[(Piperidin-4-yl)oxy]pyrimidin-5-yl}benzonitrileYield 100.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trifluoroacetic acid (1.5 ml) was added to a methylene chloride solution (2.0 ml) of 2-(1-t-butoxycarbonylpiperidin-4-yloxy)-5-(4-cyanophenyl)pyrimidine (122 mg, 0.32 mmol) at room temperature, and stirred for 2.5 hours at the temperature. The reaction solution was concentrated under reduced pressure, and the residue was extracted with chloroform. The organic layer was washed with aqueous saturated sodium bicarbonate solution and saturated saline solution in that order, dried with anhydrous sodium sulfate, and concentrated under reduced pressure to obtain the entitled compound (90 mg, 100%).

Workup

  1. concentrationThe reaction solution was concentrated under reduced pressure
  2. extractionthe residue was extracted with chloroform
  3. washThe organic layer was washed with aqueous saturated sodium bicarbonate solution and saturated saline solution in that order
  4. dry with materialdried with anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-c031c6a3c5e14a6a9ea1dfa87283028f
Source dataset
uspto-grants-2011_10
Patent number
US08044070B2

Reaction notes

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