Morpholine → HCID 57474473, compound

HRID 552974Notes

Reaction equation

HRID 552974 reaction equation
Cl[CH2:2][CH2:3][CH2:4][N:5]1[C:13]2[C:8](=[CH:9][CH:10]=[C:11]([N+:14]([O-:16])=[O:15])[CH:12]=2)[CH:7]=[CH:6]1.C([O-])([O-])=O.[K+].[K+].[NH:23]1[CH2:28][CH2:27][O:26][CH2:25][CH2:24]1>CC#N>[N:23]1([CH2:2][CH2:3][CH2:4][N:5]2[C:13]3[C:8](=[CH:9][CH:10]=[C:11]([N+:14]([O-:16])=[O:15])[CH:12]=3)[CH:7]=[CH:6]2)[CH2:28][CH2:27][O:26][CH2:25][CH2:24]1

Participants

5

Reactant 3

HCID 8083MorpholineHCID 11430Potassium CarbonateHCID 57474472HCID 57474472, compound

Product 1

HCID 57474473HCID 57474473, compoundYield 100.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of compound 148 (2.35 g, 9.845 mmol) in dry CH3CN (40 mL) was treated with K2CO3 (13.6 g, 98.458 mmol), KI (16.3 g, 98.458 mmol) and morpholine (8.58 mL, 98.458 mmol) at room temperature. The resulting mixture was refluxed for overnight (15 h). The reaction was brought to room temperature and the solvent was evaporated. The mixture was diluted with water (100 mL) and extracted with ethyl acetate (2×50 mL). The combined ethyl acetate layer was washed with water (25 mL), brine (20 mL) and dried (Na2SO4). The solvent was evaporated under reduced pressure and the crude product was purified by column chromatography (EtOAC: 2M NH3 in methanol/CH2Cl2, 1:1) to obtain compound 149 (2.85 g, quantitative) as a syrup. 1H-NMR (CDCl3) δ 1.97-2.06 (m, 2H), 2.23 (t, 2H, J=6.3 Hz), 2.38 (brs, 4H), 3.75 (t, 4H, J=4.5 Hz), 4.33 (t, 2H, J=6.6 Hz), 6.59 (d, 1H, J=3.0 Hz), 7.39 (d, 1H, J=3.0 Hz), 7.64 (d, 1H, J=8.7 Hz), 8.00 (dd, 1H, J=1.8, 8.7 Hz), 8.42 (brs, 1H).

Workup

  1. temperatureThe resulting mixture was refluxed for overnight (15 h)
  2. customwas brought to room temperature
  3. customthe solvent was evaporated
  4. additionThe mixture was diluted with water (100 mL)
  5. extractionextracted with ethyl acetate (2×50 mL)
  6. washThe combined ethyl acetate layer was washed with water (25 mL), brine (20 mL)
  7. dry with materialdried (Na2SO4)
  8. customThe solvent was evaporated under reduced pressure
  9. customthe crude product was purified by column chromatography (EtOAC: 2M NH3 in methanol/CH2Cl2, 1:1)

Sources & evidence

ORD record
ord-ca30136fee0d44e2bed3109d95fe2856
Source dataset
uspto-grants-2011_05
Patent number
US07951940B2

Reaction notes

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