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

HRID 1835246Notes

Reaction equation

HRID 1835246 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-23d02fec17ad4236a72d30e037e92217
Source dataset
uspto-grants-2004_08
Patent number
US06770650B2

Reaction notes

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