methyl 4-(4-nitro-2,3-dihydro-1H-inden-1-yl)piperazine-1-carboxylate → methyl 4-(4-amino-2,3-dihydro-1H-inden-1-yl)piperazine-1-carboxylate

HRID 1958091Notes

Reaction equation

HRID 1958091 reaction equation
[N+:1]([C:4]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:5]=1[CH2:6][CH2:7][CH:8]2[N:13]1[CH2:18][CH2:17][N:16]([C:19]([O:21][CH3:22])=[O:20])[CH2:15][CH2:14]1)([O-])=O>[Fe].CC(O)=O>[NH2:1][C:4]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:5]=1[CH2:6][CH2:7][CH:8]2[N:13]1[CH2:14][CH2:15][N:16]([C:19]([O:21][CH3:22])=[O:20])[CH2:17][CH2:18]1

Participants

4

Reactant 1

HCID 59302725methyl 4-(4-nitro-2,3-dihydro-1H-inden-1-yl)piperazine-1-carboxylate

Product 1

HCID 59302728methyl 4-(4-amino-2,3-dihydro-1H-inden-1-yl)piperazine-1-carboxylateYield 92.1%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 176Acetic AcidSolvent

Procedure

To a room temperature solution of methyl 4-(4-nitro-2,3-dihydro-1H-inden-1-yl)piperazine-1-carboxylate (216 mg, 0.71 mmol, 1.0 equiv) in MeOHH (2.8 mL) and glacial HOAc (2.8 mL) was added iron powder (198 mg, 3.54 mmol, 5.0 equiv) as a solid in one portion. After stirring overnight, the reaction mixture was concentrated in vacuo and then diluted with EtOAc and 3 N NaOH. The organic layer was washed with brine and concentrated in vacuo to provide the title compound as a brown oil (180 mg, 92%).

Workup

  1. concentrationthe reaction mixture was concentrated in vacuo
  2. additiondiluted with EtOAc and 3 N NaOH
  3. washThe organic layer was washed with brine
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-e5bb028ec5034d2db61321d0b3067455
Source dataset
uspto-grants-2013_04
Patent number
US08410108B2

Reaction notes

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