8-(4-Nitrophenyl)-1,4-dioxa-8-azaspiro[4.5]decane → 4-(1,4-Dioxa-8-azaspiro[4.5]decan-8-yl)aniline

HRID 1794840Notes

Reaction equation

HRID 1794840 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([N:10]2[CH2:19][CH2:18][C:13]3([O:17][CH2:16][CH2:15][O:14]3)[CH2:12][CH2:11]2)=[CH:6][CH:5]=1)([O-])=O.[H][H]>C(O)C.C(Cl)Cl.[Pd]>[O:14]1[C:13]2([CH2:18][CH2:19][N:10]([C:7]3[CH:8]=[CH:9][C:4]([NH2:1])=[CH:5][CH:6]=3)[CH2:11][CH2:12]2)[O:17][CH2:16][CH2:15]1

Participants

5

Reactant 2

HCID 71470798-(4-Nitrophenyl)-1,4-dioxa-8-azaspiro[4.5]decaneHCID 178418361HCID 178418361, compound

Product 1

HCID 222203164-(1,4-Dioxa-8-azaspiro[4.5]decan-8-yl)anilineYield 90%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 21584144Dichloromethane ethanolSolvent

Procedure

A mixture of 8-(4-nitro-phenyl)-1,4-dioxa-8-aza-spiro[4.5]decane (Synthesis, 606, 1981) (3.5 g, 13.3 mmol) and 10% Pd/C (0.5 g) in 100 mL of ethanol/methylene chloride (2:1) was pressurized with 30 psi hydrogen and shaken over 1 hours. The catalyst was then removed by filtering through a short pad of silica gel to give the title compound (2.8 g, 90%) as a grey solid; 1H NMR (300 MHz, DMSO-d6) δ 1.85–2.00 (m, 4 H), 3.00–3.10 (m, 4 H), 3.93 (s, 4 H), 6.60 (d, J=6.0 Hz, 2 H), 6.80 (d, J=6.0 Hz, 2 H); MS (ES) m/z: 235.2 (MH+); HRMS Calcd. for C13H18N2O2: 234.1380. Found: 234.1371.

Workup

  1. customThe catalyst was then removed
  2. filtrationby filtering through a short pad of silica gel

Sources & evidence

ORD record
ord-8ec30bb75f81489695554dbfdf2cedbb
Source dataset
uspto-grants-2006_04
Patent number
US07022716B2

Reaction notes

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