Sodium Hydroxide → 4-Boc-2-methyl-1-phenylpiperazine

HRID 2416656Notes

Reaction equation

HRID 2416656 reaction equation
[CH3:1][CH:2]1[N:7]([C:8]2[CH:13]=[CH:12][C:11](N)=[CH:10][CH:9]=2)[CH2:6][CH2:5][N:4]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:3]1.N([O-])=O.[Na+].[OH-].[Na+]>[PH2](O)=O.O.[Cu-]=O>[CH3:1][CH:2]1[N:7]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH2:6][CH2:5][N:4]([C:15]([O:17][C:18]([CH3:19])([CH3:21])[CH3:20])=[O:16])[CH2:3]1

Participants

7

Reactant 3

HCID 14798Sodium HydroxideHCID 22633057(+/-)-tert-Butyl 3-methyl-4-(4-aminophenyl)piperazine-1-carboxylateHCID 23668193Sodium Nitrite

Product 1

HCID 226330714-Boc-2-methyl-1-phenylpiperazine

Reagents, catalysts & solvents 3

HCID 178419072HCID 178419072, compoundCatalystHCID 962WaterSolventHCID 4124402Phosphinic AcidSolvent

Procedure

To a solution of (±)-tert-butyl 3-methyl-4-(4-aminophenyl)piperazine-1-carboxylate (325 mg) in 50% hypophosphorous acid (1.27 ml) containing copper(I) oxide (8.0 mg) was added dropwise a solution of sodium nitrite (92 mg) in water (2 ml) at 0° C. with stirring. After 2 hours, the reaction mixture was made alkaline with 40% NaOH solution and extracted with ethyl acetate twice. The organic layers were combined and washed with water and brine. The solvent was evaporated, and the residue was purified by silica gel column chromatography (hexane-ethyl acetate 1:1) to give the title compound in a pure form as colorless oil.

Workup

  1. extractionextracted with ethyl acetate twice
  2. washwashed with water and brine
  3. customThe solvent was evaporated
  4. customthe residue was purified by silica gel column chromatography (hexane-ethyl acetate 1:1)

Sources & evidence

ORD record
ord-af3dad8bbe5a48e8995131070a264a16
Source dataset
uspto-grants-2004_11
Patent number
US06825200B1

Reaction notes

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