2,3-Dihydro-1'-methyl-5-nitrospiro[benzofuran-3,4'-piperidine] → 5-Amino-2,3-dihydro-1'-methylspiro[benzofuran-3,4'-piperidine]

HRID 1741032Notes

Reaction equation

HRID 1741032 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][C:5]2([C:11]3[CH:12]=[C:13]([N+:16]([O-])=O)[CH:14]=[CH:15][C:10]=3[O:9][CH2:8]2)[CH2:4][CH2:3]1>[Pd].C(O)C>[NH2:16][C:13]1[CH:14]=[CH:15][C:10]2[O:9][CH2:8][C:5]3([CH2:6][CH2:7][N:2]([CH3:1])[CH2:3][CH2:4]3)[C:11]=2[CH:12]=1

Participants

4

Reactant 1

HCID 105385022,3-Dihydro-1'-methyl-5-nitrospiro[benzofuran-3,4'-piperidine]

Product 1

HCID 107275565-Amino-2,3-dihydro-1'-methylspiro[benzofuran-3,4'-piperidine]Yield 60%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

2,3-Dihydro-1'-methyl-5-nitrospiro[benzofuran-3,4'-piperidine] (D4, 0.98 g, 4.0 mmol) was hydrogenated over 10% palladium on charcoal (0.18 g) in ethanol (50 ml) for 6 h. Catalyst was filtered off onto kieselguhr, and the filtrated was evaporated and chromatographed on silica gel, eluting with 0-25% methanol/chloroform (gradient), to give the title compound (0.52 g, 60%) as a cream solid.

Workup

  1. filtrationCatalyst was filtered off onto kieselguhr
  2. customthe filtrated was evaporated
  3. customchromatographed on silica gel
  4. washeluting with 0-25% methanol/chloroform (gradient)

Sources & evidence

ORD record
ord-e7a6f32756cf4ce281af1e7a1d988818
Source dataset
uspto-grants-1999_10
Patent number
US05972951

Reaction notes

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