HCID 66711551, compound → HCID 58071351, compound

HRID 1261944Notes

Reaction equation

HRID 1261944 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([N:10]2[CH2:15][CH2:14][CH:13]([N:16]3[CH2:21][CH2:20][O:19][CH2:18][CH2:17]3)[CH2:12][CH2:11]2)[CH:7]=[CH:8][CH:9]=1)([O-])=O.[H][H]>CO.[Pd]>[N:16]1([CH:13]2[CH2:14][CH2:15][N:10]([C:6]3[CH:5]=[C:4]([NH2:1])[CH:9]=[CH:8][CH:7]=3)[CH2:11][CH2:12]2)[CH2:21][CH2:20][O:19][CH2:18][CH2:17]1

Participants

5

Reactant 2

HCID 66711551HCID 66711551, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 58071351HCID 58071351, compoundYield 42.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

4-[1-(3-Nitro-phenyl)-piperidin-4-yl]-morpholine (1.60 g, 0.00549 mol) was dissolved in Methanol (45 mL) and the solution was carefully added to Palladium on Carbon 10% (90.10, carbon black. Palladium, 0.750 g) in a Parr vessel under nitrogen. The mixture was then placed on a Parr hydrogenator and was allowed to shake until uptake of hydrogen had ceased (˜3 hours). The catalyst was then removed via filtration and the filtrate was reduced to afford 615 mg of 3-(4-Morpholin-4-yl-piperidin-1-yl)-phenylamine without further purification. 1H NMR (400 MHz, DMSO, d6) δ 6.81 (t, 1H, J=7.88 Hz), 6.14 (m, 1H), 6.11 (m, 1H), 6.00 (m, 1H), 4.80 (s, 2H), 3.57 (m, 6H), 2.46 (m, 5H), 1.82 (m, 2H), 1.43 (m, 2H).

Workup

  1. custom(˜3 hours)
  2. customThe catalyst was then removed via filtration

Sources & evidence

ORD record
ord-601bad208d5c4709971138da3e56ed13
Source dataset
uspto-grants-2013_06
Patent number
US08471005B2

Reaction notes

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