Sodium Hydroxide → 2-(4-BOC-PIPERAZINYL)-2-PHENYLACETIC ACID

HRID 1376029Notes

Reaction equation

HRID 1376029 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([CH:14]([C:21]([O:23]C)=[O:22])[C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[OH-].[Na+]>CCO>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][N:11]([CH:14]([C:21]([OH:23])=[O:22])[C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH2:12][CH2:13]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 23386132tert-Butyl 4-(2-methoxy-2-oxo-1-phenylethyl)piperazine-1-carboxylate

Product 1

HCID 27622172-(4-BOC-PIPERAZINYL)-2-PHENYLACETIC ACIDYield 86.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To 4-(Methoxycarbonyl-phenyl-methyl)-piperazine-1-carboxylic acid tert-butyl ester (151) (30.4 g, 87.25 mmol) in EtOH (200 mL) was added of 1N NaOH (192 mL) and the reaction mixture was allowed to stir at room temperature for 18 h. The reaction mixture is then concentrated to dryness. The resulting residue is taken up in H2O and acidified slowly at 0° C. with 10% NaSO4 (pH=5–6). The desired product was then extracted into EtOAc. The organic phase was then concentrated to dryness yielding 24.3 g (86%) product.

Workup

  1. concentrationThe reaction mixture is then concentrated to dryness
  2. customacidified slowly at 0° C. with 10% NaSO4 (pH=5–6)
  3. extractionThe desired product was then extracted into EtOAc
  4. concentrationThe organic phase was then concentrated to dryness

Sources & evidence

ORD record
ord-be94f9d76e8f41ebb907bb3e24e6e3e8
Source dataset
uspto-grants-2007_01
Patent number
US07169777B2

Reaction notes

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