1'-[2-Chloro-5-(methyloxy)-4-nitrophenyl]-1,4'-bipiperidine → 4-(1,4'-Bipiperidin-1'-yl)-5-chloro-2-(methyloxy)aniline

HRID 419416Notes

Reaction equation

HRID 419416 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([N+:8]([O-])=O)[C:5]([O:11][CH3:12])=[CH:4][C:3]=1[N:13]1[CH2:18][CH2:17][CH:16]([N:19]2[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]2)[CH2:15][CH2:14]1>CCO.[Pt]>[N:19]1([CH:16]2[CH2:15][CH2:14][N:13]([C:3]3[C:2]([Cl:1])=[CH:7][C:6]([NH2:8])=[C:5]([O:11][CH3:12])[CH:4]=3)[CH2:18][CH2:17]2)[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]1

Participants

4

Reactant 1

HCID 594529741'-[2-Chloro-5-(methyloxy)-4-nitrophenyl]-1,4'-bipiperidine

Product 1

HCID 594526194-(1,4'-Bipiperidin-1'-yl)-5-chloro-2-(methyloxy)aniline

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 702EthanolSolvent

Procedure

1′-[2-Chloro-5-(methyloxy)-4-nitrophenyl]-1,4′-bipiperidine was dissolved in EtOH and 5% sulfided platinum on carbon 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. TLC and MS showed the reaction was complete. The catalyst was filtered off and the filtrate was concentrated in vacuo to give the title compound of step D without further purification (2.36 g, 96%). 1H NMR (400 MHz, DMSO-d6) δ ppm 6.56-6.62 (m, 2H), 4.57 (br. s, 2H), 3.70 (d, J=1.3 Hz, 3H), 3.06 (d, J=10.6 Hz, 2H), 2.52 (t, J=11.5 Hz, 2H), 2.39-2.44 (m, 4H), 2.24 (t, J=13.8 Hz, 1H), 1.70 (d, J=11.5 Hz, 2H), 1.54 (t, J=12.4 Hz, 2H), 1.41-1.48 (m, 4H), 1.30-1.38 (m, 2H).

Workup

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

Sources & evidence

ORD record
ord-390c92682cd84bd7b2e57ba47cd2d400
Source dataset
uspto-grants-2012_01
Patent number
US08093239B2

Reaction notes

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