4-(2-((4-Nitronaphthalen-1-yl)oxy)ethyl)morpholine → 4-(2-Morpholinoethoxy)naphthalen-1-amine

HRID 1171251Notes

Reaction equation

HRID 1171251 reaction equation
[N+:1]([C:4]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[C:7]([O:14][CH2:15][CH2:16][N:17]2[CH2:22][CH2:21][O:20][CH2:19][CH2:18]2)=[CH:6][CH:5]=1)([O-])=O>[Pd].CO>[N:17]1([CH2:16][CH2:15][O:14][C:7]2[C:8]3[C:13](=[CH:12][CH:11]=[CH:10][CH:9]=3)[C:4]([NH2:1])=[CH:5][CH:6]=2)[CH2:22][CH2:21][O:20][CH2:19][CH2:18]1

Participants

4

Reactant 1

HCID 119912044-(2-((4-Nitronaphthalen-1-yl)oxy)ethyl)morpholine

Product 1

HCID 110439124-(2-Morpholinoethoxy)naphthalen-1-amineYield 81.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of 4-[2-(4-nitro-naphthalen-1-yloxy)-ethyl]-morpholine (10 g, 33.0 mmol), MeOH (80 ml) and Pd/C (10%, 1.0 g) is shaken under a hydrogen atmosphere at 30 psi for 4 hours. The mixture is then filtered through a bed of Celite under a stream of nitrogen. The filtrate is reduced under vacuum to give 4-(2-morpholin-4-yl-ethoxy)-naphthalen-1-ylamine (7.32 g, 81.3%). 1H NMR (300 MHz, CDCl3) δ 8.21 (m, 1H), 7.81 (m, 1H), 7.49 (m, 2H), 6.69 (s, 2H), 4.23 (t, 2 H), 3.76 (t, 4H), 2.92 (t, 2H), 2.65 (t, 4H). MS: 273 (M+1).

Workup

  1. filtrationThe mixture is then filtered through a bed of Celite under a stream of nitrogen

Sources & evidence

ORD record
ord-7f4a5ff9ca9e435ab2f522f019322e5b
Source dataset
uspto-grants-2010_11
Patent number
US07829560B2

Reaction notes

Loading…