Morpholine → HCID 58269171, compound

HRID 1476189Notes

Reaction equation

HRID 1476189 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[O:8][C:7]([CH2:12]Br)=[C:6]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[C:5]2=[O:20].[NH:21]1[CH2:26][CH2:25][O:24][CH2:23][CH2:22]1>C1COCC1.C(=O)(O)[O-]>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[O:8][C:7]([CH2:12][N:21]1[CH2:26][CH2:25][O:24][CH2:23][CH2:22]1)=[C:6]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[C:5]2=[O:20]

Participants

5

Reactant 2

HCID 8083MorpholineHCID 53234290HCID 53234290, compound

Product 1

HCID 58269171HCID 58269171, compoundYield 131.3%

Reagents, catalysts & solvents 2

HCID 769Bicarbonate IonSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of Intermediate 3 (0.30 g, 0.761 mmoles) in THF (2 ml), was added morpholine (0.066 g, 0.761 mmoles) at RT and refluxed for 12 h. The reaction mixture was cooled, diluted with aqueous bicarbonate solution and extracted with ethyl acetate. The organic layer was dried over sodium sulphate and concentrated under reduced pressure. The crude product was purified by column chromatography with ethyl acetate: petroleum ether to afford the title compound as off-white solid (0.40 g, 79% yield). 1H-NMR (δ ppm, DMSO-D6, 400 MHz): δ 8.12(d, J=2.2Hz, 1H), 7.98(dd, J=8.8,2.3 Hz, 1H), 7.72 (d, J=8.9 Hz, 1H), 7.45-7.39(m, 3H), 7.29(d, J=7.0Hz, 2H), 3.50(t, J=4.2Hz, 4H), 3.40(s, 2H), 2.32(br S, 4H).

Workup

  1. temperaturerefluxed for 12 h
  2. temperatureThe reaction mixture was cooled
  3. extractionextracted with ethyl acetate
  4. dry with materialThe organic layer was dried over sodium sulphate
  5. concentrationconcentrated under reduced pressure
  6. customThe crude product was purified by column chromatography with ethyl acetate

Sources & evidence

ORD record
ord-b0f28893fa0d45debd0f22b593457f7f
Source dataset
uspto-grants-2015_04
Patent number
US09018375B2

Reaction notes

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