Morpholine → HCID 19363456, compound

HRID 850517Notes

Reaction equation

HRID 850517 reaction equation
[CH3:1][O:2][C:3]1[CH:13]=[CH:12][C:6]([CH:7]=[CH:8][C:9]([OH:11])=O)=[CH:5][C:4]=1[O:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19].O.ON1C2C=CC=CC=2N=N1.[NH:31]1[CH2:36][CH2:35][O:34][CH2:33][CH2:32]1.CCN=C=NCCCN(C)C.Cl.C(=O)([O-])O.[Na+]>CN(C=O)C.C(OCC)(=O)C>[CH2:15]([O:14][C:4]1[CH:5]=[C:6](/[CH:7]=[CH:8]/[C:9]([N:31]2[CH2:36][CH2:35][O:34][CH2:33][CH2:32]2)=[O:11])[CH:12]=[CH:13][C:3]=1[O:2][CH3:1])[CH2:16][CH2:17][CH2:18][CH3:19]

Participants

8

Reactant 5

HCID 8083MorpholineHCID 516892Sodium BicarbonateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 53944971HCID 53944971, compound

Product 1

HCID 19363456HCID 19363456, compoundYield 49.8%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

4-Methoxy-3-pentyloxycinnamic acid (500 mg, 2.62 mmol, 1 eq) and 1-hydroxybenzotriazole hydrate (371 mg, 2.75 mmol, 1.05 eq) were dissolved in DMF (5 ml), and to this solution were successively added morpholine (684 mg, 7.85 mmol, 3.0 eq) and WSC hydrochloride (526 mg, 2.75 mmol, 1.05 eq) under ice-cooling. The mixture was stirred at room temperature for 12 hours. Ice water (5 ml) and a saturated aqueous sodium hydrogencarbonate solution (5 ml) were successively added to this reaction mixture. The mixture was exracted twice with ethyl acetate (20 ml). The organic layers were combined, washed with saturated brine (40 ml) and dried over anhydrous sodium sulfate. The drying agent was filtered off, and the filtrate was concentrated under reduced pressure. The obtained residue was purified by column chromatography on silica gel (n-hexane/ethyl acetate=1/2) to give (E)-3-(3-pentyloxy-4-methoxyphenyl)-1-morpholin-4-yl-prop-2-en-1-one (343 mg, 49.8%) as a colorless solid.

Workup

  1. temperaturecooling
  2. washwashed with saturated brine (40 ml)
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationThe drying agent was filtered off
  5. concentrationthe filtrate was concentrated under reduced pressure
  6. customThe obtained residue was purified by column chromatography on silica gel (n-hexane/ethyl acetate=1/2)

Sources & evidence

ORD record
ord-71b6df3ba84b48128d8a49a72d523fc6
Source dataset
uspto-grants-2000_01
Patent number
US06017919

Reaction notes

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