Ethyl Acetate → 4-(1,4'-Bipiperidin-1'-yl)-2,5-bis(methyloxy)aniline

HRID 419418Notes

Reaction equation

HRID 419418 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([N+:9]([O-])=O)[C:6]([O:12][CH3:13])=[CH:5][C:4]=1[N:14]1[CH2:19][CH2:18][CH:17]([N:20]2[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]2)[CH2:16][CH2:15]1.CCOC(C)=O>CCO.[Pt]>[N:20]1([CH:17]2[CH2:16][CH2:15][N:14]([C:4]3[C:3]([O:2][CH3:1])=[CH:8][C:7]([NH2:9])=[C:6]([O:12][CH3:13])[CH:5]=3)[CH2:19][CH2:18]2)[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]1

Participants

5

Reactant 2

HCID 8857Ethyl AcetateHCID 594525701'-[2,5-Bis(methyloxy)-4-nitrophenyl]-1,4'-bipiperidine

Product 1

HCID 594526104-(1,4'-Bipiperidin-1'-yl)-2,5-bis(methyloxy)aniline

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 702EthanolSolvent

Procedure

1′-[2,5-Bis(methyloxy)-4-nitrophenyl]-1,4′-bipiperidine (3.0 g, 8.6 mmol) was taken up in EtOH (50 mL) and EtOAc was added to help with solubility. The catalyst, 5% sulfided platinum on carbon (300 mg) was added. The reaction was placed on a Fischer-Porter Hydrogenator under 50 psi of H2 gas and was allowed to stir at rt overnight. The catalyst was filtered off and the filtrate was concentrated in vacuo to give the title compound of step B without further purification (2.72 g, 99%). 1H NMR (400 MHz, DMSO-d6) δ ppm 6.42 (s, 1H), 6.28 (s, 1H), 4.31 (s, 2H), 3.63 (s, 3H), 3.61 (s, 3H), 3.15 (d, J=11.4 Hz, 2H), 2.38-2.47 (m, 6H), 2.20 (t, J=11.5 Hz, 1H), 1.67 (d, J=11.7 Hz, 2H), 1.41-1.53 (m, 6H), 1.34 (d, J=4.8 Hz, 2H).

Workup

  1. filtrationThe catalyst was filtered off
  2. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-3c8e496b01cb4aa58174960b09e2b9fe
Source dataset
uspto-grants-2012_01
Patent number
US08093239B2

Reaction notes

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