1-Morpholinocyclopentene → HCID 22462438, compound

HRID 1936988Notes

Reaction equation

HRID 1936988 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([N:9]=[C:10]=[O:11])[CH:6]=[CH:7][CH:8]=1.O1CCN([C:18]2[CH2:22][CH2:21][CH2:20][CH:19]=2)CC1>C(Cl)(Cl)Cl.S(=O)(=O)(O)O.O>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]2[C:18]3[CH2:22][CH2:21][CH2:20][C:19]=3[C:10](=[O:11])[NH:9][C:5]=2[CH:4]=1

Participants

6

Reactant 2

HCID 702941-MorpholinocyclopenteneHCID 878433-Methoxyphenyl isocyanate

Product 1

HCID 22462438HCID 22462438, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 1118Sulfuric AcidSolventHCID 6212ChloroformSolvent

Procedure

A solution of 3-methoxyphenylisocyanate (25.0 g, 168 mmol) in chloroform (110 ml) is mixed with 1-morpholino-1-cyclopentene (25.3 ml, 168 mmol) and refluxed for 15 minutes. The batch is concentrated by evaporation and purified by column chromatography (SiO2) with ethyl acetate-hexane: 34.8 g (87%) of cyclopentanone-2-carboxylic acid-(3-methoxyphenyl)amide: 1H-NMR (CDCl3): δ=1.80-2.55 (m, 6H), 3.18 (t, 1H), 3.81 (s, 3H), 6.68 (dd, 1H), 7.04 (ddd, 1H), 7.22 (t, 1H), 7.33 (t, 1H), 8.76 (br. s, 1H). The amide (11.6 g, 50 mmol) is stirred in concentrated sulfuric acid (40 ml) for 30 minutes at 100° C. The batch is poured onto ice water, diluted with water and extracted with ethyl acetate. The combined extracts are dried (Na2SO4) and concentrated by evaporation in a vacuum: 2.43 g (23%) of product.

Workup

  1. temperaturerefluxed for 15 minutes
  2. concentrationThe batch is concentrated by evaporation
  3. custompurified by column chromatography (SiO2) with ethyl acetate-hexane
  4. additionThe batch is poured onto ice water
  5. extractionextracted with ethyl acetate
  6. dry with materialThe combined extracts are dried (Na2SO4)
  7. concentrationconcentrated by evaporation in a vacuum

Sources & evidence

ORD record
ord-7d2dec5acfcb4f63a653aedead50921a
Source dataset
uspto-grants-2002_05
Patent number
US06391887B1

Reaction notes

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