1-(3,4-Dichlorobenzyl)-4-(2-nitrocyclohexyl)piperazine → 1-(3,4-Dichlorobenzyl)-4-(2-aminocyclohexyl)piperazine

HRID 1610890Notes

Reaction equation

HRID 1610890 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:21]=[CH:22][C:23]=1[Cl:24])[CH2:5][N:6]1[CH2:11][CH2:10][N:9]([CH:12]2[CH2:17][CH2:16][CH2:15][CH2:14][CH:13]2[N+:18]([O-])=O)[CH2:8][CH2:7]1>C(O)(=O)C.[Pt](=O)=O>[Cl:1][C:2]1[CH:3]=[C:4]([CH:21]=[CH:22][C:23]=1[Cl:24])[CH2:5][N:6]1[CH2:7][CH2:8][N:9]([CH:12]2[CH2:17][CH2:16][CH2:15][CH2:14][CH:13]2[NH2:18])[CH2:10][CH2:11]1

Participants

4

Reactant 1

HCID 222577511-(3,4-Dichlorobenzyl)-4-(2-nitrocyclohexyl)piperazine

Product 1

HCID 222577361-(3,4-Dichlorobenzyl)-4-(2-aminocyclohexyl)piperazineYield 69.5%

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 176Acetic AcidSolvent

Procedure

Platinum (IV) oxide (15 mg, 0.07 mmol) was added to a solution of 1-(3,4-dichlorobenzyl)-4-(2-nitrocyclohexyl)piperazine (187 mg, 0.50 mmol) in glacial acetic acid (5 ml). The reaction mixture was stirred under hydrogen atmosphere at room temperature for 16 h. The reaction mixture was then filtered through a pad of celite. The filtrate was made basic with a 15% sodium hydroxide solution and the product was extracted into ethyl acetate. The organic layer was dried over magnesium sulfate, filtered and concentrated in vacuo to provide 1-(3,4-dichlorobenzyl)-4-(2-aminocyclohexyl)-piperazine (119 mg) as an oil.

Workup

  1. filtrationThe reaction mixture was then filtered through a pad of celite
  2. extractionthe product was extracted into ethyl acetate
  3. dry with materialThe organic layer was dried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-2da15625541241f080ad3c0cbec7f46c
Source dataset
uspto-grants-2006_01
Patent number
US06984637B2

Reaction notes

Loading…