Ethanol → HCID 66712070, compound

HRID 1262005Notes

Reaction equation

HRID 1262005 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([CH:8]2[CH2:13][CH2:12][CH2:11][N:10]([C:14]3[CH:19]=[CH:18][C:17]([N+:20]([O-])=O)=[CH:16][CH:15]=3)[CH2:9]2)[CH2:4][CH2:3]1.C(O)C.[H][H]>[Pd]>[CH3:1][N:2]1[CH2:3][CH2:4][N:5]([CH:8]2[CH2:13][CH2:12][CH2:11][N:10]([C:14]3[CH:19]=[CH:18][C:17]([NH2:20])=[CH:16][CH:15]=3)[CH2:9]2)[CH2:6][CH2:7]1

Participants

5

Reactant 3

HCID 702EthanolHCID 66711828HCID 66711828, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 66712070HCID 66712070, compoundYield 76.1%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

1-Methyl-4-[1-(4-nitro-phenyl)-piperidin-3-yl]-piperazine (1.40 g, 4.60 mmol) was dissolved in Ethanol (36.1 mL, 618 mmol) and the solution was carefully added to 10% Palladium on Carbon (0.515 g, 38.6 mmol) under nitrogen. The mixture was then placed on a Parr hydrogenation apparatus and was allowed to shake at 55 psi until uptake of hydrogen ceased. The catalyst was then filtered to afford 0.960 g of 4-[3-(4-Methyl-piperazin-1-yl)-piperidin-1-yl]-phenylamine without further purification. (M+H)=275.7. 1H NMR (400 MHz, DMSO, d6) δ 6.67 (d, 2H, J=8.56 Hz), 6.47 (d, 2H, J=8.51 Hz), 4.54 (s, 2H), 3.39 (m, 2H), 3.20 (m, 1H), 2.62 (m, 4H), 2.33 (m, 6H), 2.12 (s, 3H), 1.85 (m, 1H), 1.74 (m, 1H), 1.52 (m, 1H), 1.18 (m, 1H).

Workup

  1. filtrationThe catalyst was then filtered

Sources & evidence

ORD record
ord-486fb4c293da4117a09331bf7580f062
Source dataset
uspto-grants-2013_06
Patent number
US08471005B2

Reaction notes

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