Lithium Hydroxide → HCID 59416800, compound

HRID 1184465

Reaction equation

HRID 1184465 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 59416800HCID 59416800, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

tert-butyl 4-(2-fluoro-4-(methoxycarbonyl)phenyl)piperazine-1-carboxylate 301 (4.6 g, 13.59 mmol) was suspended in 1,4-dioxane (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. The precipitate was filtered, washed with water, and dried in vacuum to afford the title compound as a brown solid (4.40 g, 13.57 mmol, 100% yield). ESI-MS: m/z 325 (M+H)+.

Workup

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

Sources & evidence

ORD record
ord-d70a773b14cd436eb3643879360a0ead
Source dataset
uspto-grants-2014_03
Patent number
US08669249B2

Linked notes

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