Ethanol → HCID 66711339, compound

HRID 1262000Notes

Reaction equation

HRID 1262000 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([N:10]2[CH2:15][CH2:14][CH2:13][CH:12]([N:16]3[CH2:21][CH2:20][O:19][CH2:18][CH2:17]3)[CH2:11]2)=[CH:6][CH:5]=1)([O-])=O.C(O)C.[H][H]>[Pd]>[N:16]1([CH:12]2[CH2:13][CH2:14][CH2:15][N:10]([C:7]3[CH:8]=[CH:9][C:4]([NH2:1])=[CH:5][CH:6]=3)[CH2:11]2)[CH2:17][CH2:18][O:19][CH2:20][CH2:21]1

Participants

5

Reactant 3

HCID 702EthanolHCID 66711380HCID 66711380, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 66711339HCID 66711339, compoundYield 99.5%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

4-[1-(4-Nitro-phenyl)-piperidin-3-yl]-morpholine (1.30 g, 4.46 mmol) was dissolved in Ethanol (35.0 mL, 599 mmol) and the solution was carefully added to 10% Palladium on Carbon (0.500 g, 37.5 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 1.16 g of 4-(3-Morpholin-4-yl-piperidin-1-yl)-phenylamine without further purification. (M+H)=262.7. 1H NMR (400 MHz, DMSO, d6) δ 6.67 (d, 2H, J=8.72 Hz), 6.47 (d, 2H, J=10.09 Hz), 4.54 (s, 2H), 3.55 (m, 4H), 3.41 (m, 1H), 3.22 (m, 1H), 2.51 (m, 4H), 2.40 (m, 3H), 1.86 (m, 1H), 1.76 (m, 1H), 1.56 (m, 1H), 1.18 (m, 1H).

Workup

  1. filtrationThe catalyst was then filtered

Sources & evidence

ORD record
ord-69fb71680fb54211ae0c4543cf1f0128
Source dataset
uspto-grants-2013_06
Patent number
US08471005B2

Reaction notes

Loading…