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

HRID 2077978Notes

Reaction equation

HRID 2077978 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-eaf46d2e4106493e83c25b8babdc0e1e
Source dataset
uspto-grants-2011_04
Patent number
US07928105B2

Reaction notes

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