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

HRID 1641249Notes

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, 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-f0b63bb125ca4b38b0ca00dd73895410
Source dataset: uspto-grants-2012_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08114873B2

Reaction notes

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