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

HRID 1610889

Reaction equation

HRID 1610889 reaction equation
[N+:1]([C:4]1[CH2:9][CH2:8][CH2:7][CH2:6][CH:5]=1)([O-:3])=[O:2].Cl.Cl.C[CH:13]1[N:18]([CH2:19][C:20]2[CH:25]=[CH:24][C:23]([Cl:26])=[C:22]([Cl:27])[CH:21]=2)[CH2:17][CH2:16][N:15](CC(NC(=O)C2C=CC(C)=CC=2)C(C)C)[CH2:14]1.C(N(CC)CC)C>C(Cl)Cl.C(OCC)(=O)C>[Cl:27][C:22]1[CH:21]=[C:20]([CH:25]=[CH:24][C:23]=1[Cl:26])[CH2:19][N:18]1[CH2:13][CH2:14][N:15]([CH:5]2[CH2:6][CH2:7][CH2:8][CH2:9][CH:4]2[N+:1]([O-:3])=[O:2])[CH2:16][CH2:17]1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 757131-NitrocyclohexeneHCID 22257752n-{1(Rs)-[3-methyl-4-(3,4-dichlorobenzyl)piperazin-1-ylmethyl]-2-methylpropyl}-4-methylbenzamide dihydrochloride salt

Product 1

HCID 222577511-(3,4-Dichlorobenzyl)-4-(2-nitrocyclohexyl)piperazineYield 50.5%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 1-nitrocyclohexene (311 mg, 2.45 mmol), dichlorobenzylpiperazine [prepared as described in Example 1](600 mg, 2.45 mmol), and triethylamine (512 μl, 3.68 mmol) in methylene chloride (10 ml) was stirred at room temperature under nitrogen atmosphere for 17 h. The reaction mixture was diluted with ethyl acetate, washed with an aqueous sodium bicarbonate solution, dried over magnesium sulfate and concentrated in vacuo. The residue was chromatographed with hexanes/ethyl acetate (2:1) as the eluant to provide 1-(3,4-dichlorobenzyl)-4-(2-nitrocyclohexyl)piperazine (461 mg) as an oil.

Workup

  1. washwashed with an aqueous sodium bicarbonate solution
  2. dry with materialdried over magnesium sulfate
  3. concentrationconcentrated in vacuo
  4. customThe residue was chromatographed with hexanes/ethyl acetate (2:1) as the eluant

Sources & evidence

ORD record
ord-b2f72d369ac4403eb8c24bd71580a379
Source dataset
uspto-grants-2006_01
Patent number
US06984637B2

Linked notes

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