HCID 2297612, compound → HCID 23149117, compound

HRID 415095Notes

Reaction equation

HRID 415095 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([CH:15]=[CH:16][C:17]=1[N+:18]([O-])=O)[O:5][CH2:6][CH2:7][CH2:8][N:9]1[CH2:14][CH2:13][O:12][CH2:11][CH2:10]1>[Pd]>[CH3:1][C:2]1[CH:3]=[C:4]([O:5][CH2:6][CH2:7][CH2:8][N:9]2[CH2:10][CH2:11][O:12][CH2:13][CH2:14]2)[CH:15]=[CH:16][C:17]=1[NH2:18]

Participants

3

Reactant 1

HCID 2297612HCID 2297612, compound

Product 1

HCID 23149117HCID 23149117, compoundYield 32%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

An ethanolic (20 mL) solution of 4-(3-(3-methyl-4-nitrophenoxy)propyl) morpholine (0.75 g, 2.7 mmol) was subjected to hydrogenation using the H-cube (Pd/C catalyst cartridge and H2, 1-5 bar) for 1 hour. 2-Methyl-4-(3-morpholinopropoxy)aniline was isolated by concentration under reduced pressure (0.22 g, 32% yield). 1H-NMR (400 MHz DMSO-d6): δ 6.57-6.51 (m, 3H), 3.85 (t, 6.4 Hz, 2H), 3.69-3.62 (m, 4H), 3.46-3.43 (m, 2H), 2.56 (m, 4H), 2.02 (s, 3H), 1.88-1.85 (m, 2H). MS (EI): 251 (MH+).

Workup

  1. customfor 1 hour

Sources & evidence

ORD record
ord-1a413ca6fe6043f3aa5f5bc2d57d1d76
Source dataset
uspto-grants-2012_01
Patent number
US08088767B2

Reaction notes

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