HCID 57440688, compound → HCID 57440689, compound

HRID 2102345Notes

Reaction equation

HRID 2102345 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[CH2:13][N:12]([CH2:14][CH2:15][CH3:16])[C:11](=O)[CH2:10][O:9]2)=[CH:4][C:3]=1[O:18][CH3:19]>Cl>[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[O:9][CH2:10][CH2:11][N:12]([CH2:14][CH2:15][CH3:16])[CH2:13]2)=[CH:4][C:3]=1[O:18][CH3:19]

Participants

3

Reactant 1

HCID 57440688HCID 57440688, compound

Product 1

HCID 57440689HCID 57440689, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

Prepared following the same method as for example 6 starting with the morpholin-3-one from example 21 (633 mg, 2.37 mmol). After refluxing in 6M HCl (aq) the reaction mixture was cooled and extracted with diethyl ether (2×20 ml). The organic layers were discarded and the aqueous layer basified by the addition of potassium carbonate. The aqueous residue was then extracted with ethyl acetate (3×20 ml). The organic extracts were combined and dried over anhydrous magnesium sulphate, filtered and concentrated in vacuo to give the title compound as a yellow oil (552 mg, 2.18 mmol, 92%). 1H NMR (CD3OD, 400 MHz) δ: 0.95 (t, 3H), 1.58 (m, 2H), 2.02 (t, 1H), 2.22 (dt, 1H), 2.38 (t, 2H), 2.85 (d, 1H), 2.93 (d, 1H), 3.80 (m, 1H), 3.84 (s, 3H), 4.01 (dd, 1H), 4.50 (dd, 1H), 6.88 (m, 1H), 7.02 (t, 1H), 7.09 (d, 1H). LRMS: m/z 254 (M-H+).

Workup

  1. customPrepared
  2. temperaturewas cooled
  3. extractionextracted with diethyl ether (2×20 ml)
  4. additionthe aqueous layer basified by the addition of potassium carbonate
  5. extractionThe aqueous residue was then extracted with ethyl acetate (3×20 ml)
  6. dry with materialdried over anhydrous magnesium sulphate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-765748acc3f04c6ebdf4b24a11d8085e
Source dataset
uspto-grants-2009_08
Patent number
US07576081B2

Reaction notes

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