Hydrazine hydrate (1:1) → tert-Butyl trans-4-[(5-amino-1-benzofuran-7-yl)methyl]-2,5-dimethylpiperazine-1-carboxylate

HRID 1162065Notes

Reaction equation

HRID 1162065 reaction equation
[CH3:1][C@H:2]1[CH2:7][N:6]([CH2:8][C:9]2[C:17]3[O:16][CH:15]=[CH:14][C:13]=3[CH:12]=[C:11]([N+:18]([O-])=O)[CH:10]=2)[C@H:5]([CH3:21])[CH2:4][N:3]1[C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23].O.NN>C1COCC1.CCO.[Ni]>[NH2:18][C:11]1[CH:10]=[C:9]([CH2:8][N:6]2[C@H:5]([CH3:21])[CH2:4][N:3]([C:22]([O:24][C:25]([CH3:26])([CH3:28])[CH3:27])=[O:23])[C@@H:2]([CH3:1])[CH2:7]2)[C:17]2[O:16][CH:15]=[CH:14][C:13]=2[CH:12]=1

Participants

5

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 86609639tert-Butyl trans-2,5-dimethyl-4-[(5-nitro-1-benzofuran-7-yl)methyl]piperazine-1-carboxylate

Product 1

HCID 66892496tert-Butyl trans-4-[(5-amino-1-benzofuran-7-yl)methyl]-2,5-dimethylpiperazine-1-carboxylateYield 87.4%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 21873804Tetrahydrofuran ethanolSolvent

Procedure

tert-Butyl trans-2,5-dimethyl-4-[(5-nitro-1-benzofuran-7-yl)methyl]piperazine-1-carboxylate (0.14 g, 0.35 mmol; obtained in Step 2) was dissolved in THF/EtOH (4:1; 5 mL). Excess Raney-Ni (slurry in EtOH) was added followed by hydrazine hydrate (0.07 g, 1.39 mmol). The reaction mixture was stirred overnight at ambient temperature. After filtration and evaporation of solvent, a crude oil (0.11 g, 87%) was obtained that was used in the next step without further purification. HPLC 86% RT=1.15 min (System B; 10-97% MeCN over 3 min). MS (ESI+) m/z 360.2 (M+H)+.

Workup

  1. filtrationAfter filtration and evaporation of solvent

Sources & evidence

ORD record
ord-79571893d7044aae86289e29886b41ff
Source dataset
uspto-grants-2010_10
Patent number
US07820675B2

Reaction notes

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