Acetonitrile → 4-[2-(4-Nitrophenoxy)ethyl]morpholine

HRID 1261913Notes

Reaction equation

Br[CH2:2][CH2:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[CH:7][CH:6]=1.[NH:14]1[CH2:19][CH2:18][O:17][CH2:16][CH2:15]1.C(#N)C.C(=O)([O-])[O-].[K+].[K+]>>[N+:11]([C:8]1[CH:9]=[CH:10][C:5]([O:4][CH2:3][CH2:2][N:14]2[CH2:19][CH2:18][O:17][CH2:16][CH2:15]2)=[CH:6][CH:7]=1)([O-:13])=[O:12]

Participants

Reactant 4

HCID 6342Acetonitrile

HCID 8083Morpholine

HCID 11430Potassium Carbonate

HCID 2359871-(2-Bromoethoxy)-4-nitrobenzene

Product 1

HCID 8008814-[2-(4-Nitrophenoxy)ethyl]morpholineYield 84%

Conditions

Temperature: 80 °C

Procedure

Into a 30 mL vial, [A] 1-(2-Bromo-ethoxy)-4-nitro-benzene (5.00 g, 0.0203 mol), Morpholine (3.54 mL, 0.0406 mol), Acetonitrile (15.0 mL, 0.287 mol) and Potassium carbonate (5.62 g, 0.0406 mol) were added. The reaction was heated at 80° C. for 4 hours. The reaction was partitioned with water (250 mL). The solid was filtered and washed with water. The resulting solid was dried under vacuum overnight to give 4-[2-(4-Nitrophenoxy)-ethyl]-morpholine as an off-white solid (4.30 g, 84%). NMR 1H (DSMO-d6)-8.20 (d, 1H, J=9.34 Hz), 7.17 (d, 2H, J=9.34 Hz), 4.24 (t, 2H, J=5.65 Hz), 3.57 (t, 4H, J=4.60 Hz), 2.72 (t, 2H, J=4.68 Hz), 2.47 (t, 4H, J=4.52 Hz),

Workup

customThe reaction was partitioned with water (250 mL)
filtrationThe solid was filtered
washwashed with water
customThe resulting solid was dried under vacuum overnight

Sources & evidence

ORD record: ord-7b6fa4ed8b29463e969f0273a8c4191a
Source dataset: uspto-grants-2013_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08471005B2

Reaction notes

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