Hydrazine hydrate (1:1) → 1,1-Dimethylethyl 4-[(5-amino-7-benzofuranyl)methyl]-1-piperazinecarboxylate

HRID 1162045Notes

Reaction equation

HRID 1162045 reaction equation
O.NN.[N+:4]([C:7]1[CH:8]=[C:9]([CH2:16][N:17]2[CH2:22][CH2:21][N:20]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH2:19][CH2:18]2)[C:10]2[O:14][CH:13]=[CH:12][C:11]=2[CH:15]=1)([O-])=O>[Ni].C(O)C.C1COCC1>[C:26]([O:25][C:23]([N:20]1[CH2:19][CH2:18][N:17]([CH2:16][C:9]2[C:10]3[O:14][CH:13]=[CH:12][C:11]=3[CH:15]=[C:7]([NH2:4])[CH:8]=2)[CH2:22][CH2:21]1)=[O:24])([CH3:29])([CH3:27])[CH3:28]

Participants

5

Reactant 2

HCID 24654Hydrazine hydrate (1:1)2×HCID 66893515HCID 66893515, compound

Product 1

HCID 668930201,1-Dimethylethyl 4-[(5-amino-7-benzofuranyl)methyl]-1-piperazinecarboxylateYield 105.6%

Reagents, catalysts & solvents 2

HCID 935NickelCatalyst2×HCID 21873804Tetrahydrofuran ethanolSolvent

Procedure

Raney nickel (slurry in ethanol) and hydrazine hydrate (66 μL, 1.36 mmol) were added to tert-butyl 4-[(5-nitro-1-benzofuran-7-yl)methyl]piperazine-1-carboxylate (123 mg, 0.34 mmol; obtained in Step 1) in ethanol:THF (4:1; 10 mL). The mixture was stirred at room temperature for 1 h. Unreacted starting material was still present and additional Raney nickel and hydrazine hydrate (33 μL, 0.68 mmol) were added with continuos stirring for 1 h. The mixture was filtered through a pad of Celite, which was rinsed several times with ethanol. Evaporation of the solvent gave 119 mg (quantitative) of the title amine as a green sticky oil which was used directly in the next step.

Workup

  1. stirringstirring for 1 h
  2. filtrationThe mixture was filtered through a pad of Celite, which
  3. washwas rinsed several times with ethanol
  4. customEvaporation of the solvent

Sources & evidence

ORD record
ord-437752070293431c99040d212e4f2126
Source dataset
uspto-grants-2010_10
Patent number
US07820675B2

Reaction notes

Loading…