3,5-Dihydroxybenzoic Acid → HCID 21846072, compound

HRID 1597879Notes

Reaction equation

HRID 1597879 reaction equation
[C:1]([O-:4])([O-])=O.[K+].[K+].[OH:7][C:8]1[CH:9]=[C:10]([CH:14]=[C:15]([OH:17])[CH:16]=1)[C:11]([OH:13])=[O:12].Cl.Cl[CH2:20][CH2:21][N:22]1[CH2:27][CH2:26][O:25][CH2:24][CH2:23]1>CC#N>[N:22]1([CH2:21][CH2:20][O:7][C:8]2[CH:9]=[C:10]([CH:14]=[C:15]([O:17][CH2:20][CH2:21][N:22]3[CH2:27][CH2:1][O:4][CH2:24][CH2:23]3)[CH:16]=2)[C:11]([O:13][CH2:20][CH2:21][N:22]2[CH2:27][CH2:26][O:25][CH2:24][CH2:23]2)=[O:12])[CH2:27][CH2:26][O:25][CH2:24][CH2:23]1

Participants

5

Reactant 3

HCID 74243,5-Dihydroxybenzoic AcidHCID 11430Potassium CarbonateHCID 77210Morpholine, 4-(2-chloroethyl)-, hydrochloride (1:1)

Product 1

HCID 21846072HCID 21846072, compoundYield 50.3%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a suspension of K2CO3 (82.88 g, 0.6 mol) in CH3CN (300 ml) was added 3,5-dihydroxybenzoic acid (4.62 g, 0.03 mol), followed 10 minutes later by N-(2-chloroethyl)morpholine hydrochloride (18.42 g, 0.099 mol). The reaction mixture was refluxed overnight, cooled, filtered and the filtrate was concentrated in vacuo. The oily residue was purified by column chromatography on silica gel eluting with acetone, followed by Kugelrohr distillation at>195° C. and 0.2 mm Hg to afford 7.45 g of 4-morpholinylethyl 3,5-di-[2-(4-morpholinyl)ethoxy]benzoate.

Workup

  1. temperatureThe reaction mixture was refluxed overnight
  2. temperaturecooled
  3. filtrationfiltered
  4. concentrationthe filtrate was concentrated in vacuo
  5. customThe oily residue was purified by column chromatography on silica gel eluting with acetone
  6. distillationfollowed by Kugelrohr distillation at>195° C. and 0.2 mm Hg

Sources & evidence

ORD record
ord-78493e746f074892b173ea5f2f309045
Source dataset
uspto-grants-1998_04
Patent number
US05736548

Reaction notes

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