Potassium Carbonate → 4-(2-((4-Nitronaphthalen-1-yl)oxy)ethyl)morpholine

HRID 1171381Notes

Reaction equation

[N+:1]([C:4]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[C:7]([OH:14])=[CH:6][CH:5]=1)([O-:3])=[O:2].Cl.Cl[CH2:17][CH2:18][N:19]1[CH2:24][CH2:23][O:22][CH2:21][CH2:20]1.[OH-].[Na+].C(=O)([O-])[O-].[K+].[K+]>O.CN1CCCC1=O>[N+:1]([C:4]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[C:7]([O:14][CH2:17][CH2:18][N:19]2[CH2:24][CH2:23][O:22][CH2:21][CH2:20]2)=[CH:6][CH:5]=1)([O-:3])=[O:2]

Participants

Conditions

Temperature: 40 °C

Procedure

A mixture of 4-nitro-1-hydroxynaphthalene (10 g, 52.8 mmol), 4-(2-chloroethyl)-morpholine hydrochloride (13.77 g, 74.0 mmol), sodium hydroxide (3.0 g, 74.0 mmol), potassium carbonate (17.53 g, 126.8 mmol) and 1-methyl-2-pyrrolidinone (400 ml) is heated to 90°-100° C. for 2-3 hours. The mixture is cooled to 40° C. and water (300 ml) added. The mixture is then cooled to 0° C. and held for 4 hours. The product is precipitated and collected by filtration, washed with water, cyclohexane and dried under vacuum to yield 4-[2-(4-nitro-naphthalen-1-yloxy)-ethyl]-morpholine (14.73 g, 92.6%). 1H NMR 300 MHz (CDCl3) 8.80 (d, 1H), 8.38 (t, 2H), 7.75 (t, 1H), 7.63 (t, 1H), 6.84 (d, is 1H), 4.40 (t, 2H), 3.75 (t, 4H), 3.01 (t, 2H), 2.66 (t, 4H). MS: 303 (M+1).

Workup

temperatureis heated to 90°-100° C. for 2-3 hours
temperatureThe mixture is then cooled to 0° C.
customThe product is precipitated
filtrationcollected by filtration
washwashed with water, cyclohexane
customdried under vacuum

Sources & evidence

ORD record: ord-f8a463b565db40c2a8185d361af85e4b
Source dataset: uspto-grants-2010_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07829560B2

Reaction notes

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