Lithium Hydroxide → 4-(4-(Tert-butoxycarbonyl)piperazin-1-yl)-3-fluorobenzoic acid

HRID 1645037Notes

Reaction equation

HRID 1645037 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([C:8]([O:10]C)=[O:9])[CH:5]=[CH:4][C:3]=1[N:12]1[CH2:17][CH2:16][N:15]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:14][CH2:13]1.[Li+].[OH-]>O1CCOCC1>[C:21]([O:20][C:18]([N:15]1[CH2:16][CH2:17][N:12]([C:3]2[CH:4]=[CH:5][C:6]([C:8]([OH:10])=[O:9])=[CH:7][C:2]=2[F:1])[CH2:13][CH2:14]1)=[O:19])([CH3:24])([CH3:22])[CH3:23]

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 23117202Tert-butyl 4-(2-fluoro-4-(methoxycarbonyl)phenyl)piperazine-1-carboxylate

Product 1

HCID 594168004-(4-(Tert-butoxycarbonyl)piperazin-1-yl)-3-fluorobenzoic acidYield 100%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Tert-butyl 4-(2-fluoro-4-(methoxycarbonyl)phenyl)piperazine-1-carboxylate (4.6 g, 13.59 mmol) was suspended in 1,4-Dioxane (Volume: 68.0 ml) and treated with 1N LiOH (68.0 ml, 68.0 mmol). The reaction mixture was stirred at room temperature for 23 h. The reaction mixture was concentrated in vacuo until most of the dioxane was gone and acidified with HCl (4.5 N) until a thick precipitate resulted. It was filtered off, washed with water and dried in vacuum to afford 4-(4-(tert-butoxycarbonyl)piperazin-1-yl)-3-fluorobenzoic acid (4.40 g, 13.57 mmol, 100% yield) as a brown solid. ESI-MS: m/z 325 (M+H)+.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo until most of the dioxane
  2. customresulted
  3. filtrationIt was filtered off
  4. washwashed with water
  5. customdried in vacuum

Sources & evidence

ORD record
ord-b679ccd4ede94cd68761abf5ebe4ea91
Source dataset
uspto-grants-2012_02
Patent number
US08124606B2

Reaction notes

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