Sulfuric acid magnesium salt (1:1) → 1-Benzyl 4-tert-butyl 2-[(4-{[(3,4-dichlorophenyl)amino]carbonyl}piperazin-1-yl)methyl]piperazine-1,4-dicarboxylate

HRID 2371185Notes

Reaction equation

HRID 2371185 reaction equation
[CH:1]([CH:3]1[CH2:8][N:7]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:6][CH2:5][N:4]1[C:16]([O:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)=[O:17])=O.[Cl:26][C:27]1[CH:28]=[C:29]([NH:34][C:35]([N:37]2[CH2:42][CH2:41][NH:40][CH2:39][CH2:38]2)=[O:36])[CH:30]=[CH:31][C:32]=1[Cl:33].CCN(C(C)C)C(C)C.[O-]S([O-])(=O)=O.[Mg+2].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(=O)(O)[O-].[Na+]>C1COCC1.C(OCC)(=O)C>[Cl:26][C:27]1[CH:28]=[C:29]([NH:34][C:35]([N:37]2[CH2:42][CH2:41][N:40]([CH2:1][CH:3]3[CH2:8][N:7]([C:9]([O:11][C:12]([CH3:13])([CH3:14])[CH3:15])=[O:10])[CH2:6][CH2:5][N:4]3[C:16]([O:18][CH2:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)=[O:17])[CH2:39][CH2:38]2)=[O:36])[CH:30]=[CH:31][C:32]=1[Cl:33]

Participants

9

Reactant 6

HCID 24083Sulfuric acid magnesium salt (1:1)HCID 81531DiisopropylethylamineHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 16775732N-(3,4-Dichlorophenyl)piperazine-1-carboxamideHCID 596715274-Boc-1-Cbz-piperazine-2-carbaldehyde

Product 1

HCID 576568421-Benzyl 4-tert-butyl 2-[(4-{[(3,4-dichlorophenyl)amino]carbonyl}piperazin-1-yl)methyl]piperazine-1,4-dicarboxylate

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To 1-benzyl 4-tert-butyl 2-formylpiperazine-1,4-dicarboxylate (227 mg) in THF (20 ml) were added N-(3,4-dichlorophenyl)piperazine-1-carboxamide (179 mg), DIPEA (319 ul) DMF (1.6 ml) and MgSO4 (30 mg) the mixture stirred at room temperature for 30 minutes, sodium triacetoxyborohydride (277 mg) added and stirring continued for 16 hours at room temperature. Saturated aqueous sodium bicarbonate and ethyl acetate were added. The organic phase was dried (MgSO4) and evaporated to give the title compound as a semi-solid gum (331 mg, 84%).

Workup

  1. stirringstirring
  2. waitcontinued for 16 hours at room temperature
  3. dry with materialThe organic phase was dried (MgSO4)
  4. customevaporated

Sources & evidence

ORD record
ord-2d7b465bf3e04fd9af41a7f2e5641146
Source dataset
uspto-grants-2014_04
Patent number
US08710224B2

Reaction notes

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