HCID 66891987, compound → HCID 66894201, compound

HRID 1161979Notes

Reaction equation

HRID 1161979 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([N:13]2[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]2)[C:7]2[O:11][CH:10]=[CH:9][C:8]=2[CH:12]=1)([O-])=O>CCOC(C)=O.O=[Pt]=O>[N:13]1([C:6]2[C:7]3[O:11][CH:10]=[CH:9][C:8]=3[CH:12]=[C:4]([NH2:1])[CH:5]=2)[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]1

Participants

4

Reactant 1

HCID 66891987HCID 66891987, compound2×

Product 1

HCID 66894201HCID 66894201, compound

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 8857Ethyl AcetateSolvent

Procedure

1-(5-Nitro-1-benzofuran-7-yl)piperidine (630 mg, 2.56 mmol; Intermediate 4) was dissolved in EtOAc (50 mL), PtO2 added and the mixture stirred under H2 for 36 h. Filtration through Celite and concentration of the filtrate furnished 7-piperidin-1-yl-1-benzofuran-5-amine. Yield: 540 mg (98%). 1H NMR (400 MHz, CDCl3) δ ppm 1.59-1.65 (m, 2H), 1.71-1.83 (m, 4H), 3.21-3.26 (m, 4H), 3.55 (br s, 2H), 6.19 (d, 1H), 6.45 (d, 1H), 6.56 (d, 1H), 7.51 (d, 1H); GC-MS (EI+) for C13H16N2O m/z 216 M+.

Workup

  1. filtrationFiltration through Celite and concentration of the filtrate

Sources & evidence

ORD record
ord-dc7142abec8c4094a3a9e10016846dfc
Source dataset
uspto-grants-2010_10
Patent number
US07820675B2

Reaction notes

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