Potassium Carbonate → 1-(2-Morpholin-4-ylethyl)-7-nitro-1,2,3,4-tetrahydroquinoline

HRID 494179Notes

Reaction equation

[N+:1]([C:4]1[CH:13]=[C:12]2[C:7]([CH2:8][CH2:9][CH2:10][NH:11]2)=[CH:6][CH:5]=1)([O-:3])=[O:2].C(=O)([O-])[O-].[K+].[K+].I[CH2:21][CH2:22][N:23]1[CH2:28][CH2:27][O:26][CH2:25][CH2:24]1>CN(C=O)C.O>[N:23]1([CH2:22][CH2:21][N:11]2[C:12]3[C:7](=[CH:6][CH:5]=[C:4]([N+:1]([O-:3])=[O:2])[CH:13]=3)[CH2:8][CH2:9][CH2:10]2)[CH2:28][CH2:27][O:26][CH2:25][CH2:24]1

Participants

Conditions

Temperature: 70 °C

Procedure

To a solution of 7-nitro-1,2,3,4-tetrahydroquinoline (D1) (246 mg, 1.38 mmol) in DMF (2.7 ml) was added potassium carbonate (574 mg, 4.15 mmol) followed by a solution of 4-(2-iodoethyl)morpholine (500 mg, 2.07 mmol) in DMF (2 ml) and the reaction heated to 70° C. After cooling to ambient temperature the reaction mixture was diluted with water and extracted with EtOAc which was washed with water, dried over MgSO4 and concentrated in vacuo to give the crude product which was purified by silica SPE chromatography. Elution with 80% EtOAc/petroleum ether gave the title compound as an orange gum (29 mg). 1H NMR (250 MHz, CDCl3) δ (ppm): 7.39 (m, 2H), 7.00 (d, 1H), 3.73 (m, 4H), 3.47 (m, 2H), 3.38 (m, 2H), 2.79 (t, 2H), 2.49-2.59 (m, 6H), 1.96 (m, 2H).

Workup

temperatureAfter cooling to ambient temperature the reaction mixture
extractionextracted with EtOAc which
washwas washed with water
dry with materialdried over MgSO4
concentrationconcentrated in vacuo
customto give the crude product which
customwas purified by silica SPE chromatography
washElution with 80% EtOAc/petroleum ether

Sources & evidence

ORD record: ord-c1f11253054c41899e4cbefe6415ca3c
Source dataset: uspto-grants-2009_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07538121B2

Reaction notes

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