Trifluoroacetic acid → 4-{4-[2-fluoro-3-(hydroxymethyl)phenyl]piperazin-1-yl}pyridin-2(1H)-one

HRID 1021299Notes

Reaction equation

HRID 1021299 reaction equation
C([O:5][C:6]1[CH:11]=[C:10]([N:12]2[CH2:17][CH2:16][N:15]([C:18]3[CH:23]=[CH:22][CH:21]=[C:20]([CH2:24][O:25][Si](C(C)(C)C)(C)C)[C:19]=3[F:33])[CH2:14][CH2:13]2)[CH:9]=[CH:8][N:7]=1)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[F:33][C:19]1[C:20]([CH2:24][OH:25])=[CH:21][CH:22]=[CH:23][C:18]=1[N:15]1[CH2:16][CH2:17][N:12]([C:10]2[CH:9]=[CH:8][NH:7][C:6](=[O:5])[CH:11]=2)[CH2:13][CH2:14]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86686242HCID 86686242, compound

Product 1

HCID 683098694-{4-[2-fluoro-3-(hydroxymethyl)phenyl]piperazin-1-yl}pyridin-2(1H)-oneYield 87.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1-(2-tert-Butoxypyridin-4-yl)-4-[3-({[tert-butyl(dimethyl)silyl]oxy}methyl)-2-fluorophenyl]piperazine (3.14 g) was mixed with CH2Cl2 (50 ml), and TFA (5.1 ml) was added thereto, followed by stirring at room temperature overnight. The reaction mixture was concentrated under reduced pressure, and the residue was mixed with MeOH (2 ml). A 8 M NH3/MeOH solution (10 ml) was added thereto at 0° C., followed by stirring at room temperature for 2 hours. The solid in the reaction mixture was collected by filtration, washed with MeOH, and dried at 50° C. under reduced pressure to obtain 4-{4-[2-fluoro-3-(hydroxymethyl)phenyl]piperazin-1-yl}pyridin-2(1H)-one (1.76 g).

Workup

  1. additionwas added
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. additionthe residue was mixed with MeOH (2 ml)
  4. additionA 8 M NH3/MeOH solution (10 ml) was added
  5. customat 0° C.
  6. stirringby stirring at room temperature for 2 hours
  7. filtrationThe solid in the reaction mixture was collected by filtration
  8. washwashed with MeOH
  9. customdried at 50° C. under reduced pressure

Sources & evidence

ORD record
ord-42cec8aababa4bd8841302b239025bf2
Source dataset
uspto-grants-2014_05
Patent number
US08716470B2

Reaction notes

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