Diethyl Ether → HCID 12937986, compound

HRID 2413780Notes

Reaction equation

HRID 2413780 reaction equation
[CH3:1][O:2][C:3](=[O:16])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([C:10]2[CH:11]=[N:12][CH:13]=[CH:14][CH:15]=2)[CH:5]=1.C(N(CC)CC)C.[C:24](Cl)(=[O:27])[CH2:25][CH3:26].CCOCC>CO.O=[Pt]=O>[CH3:1][O:2][C:3](=[O:16])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([CH:10]2[CH2:15][CH2:14][CH2:13][N:12]([C:24](=[O:27])[CH2:25][CH3:26])[CH2:11]2)[CH:5]=1

Participants

7

Reactant 4

HCID 3283Diethyl EtherHCID 8471TriethylamineHCID 62324Propionyl chlorideHCID 4133188Methyl 3-(3-pyridinyl)benzoate

Product 1

HCID 12937986HCID 12937986, compoundYield 79.2%

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 887MethanolSolvent

Procedure

A solution of the HCl-salt of methyl-3-(3-pyridyl)benzoate (5.54 g, 0.022 mol) in methanol was hydrogenated (atm. pressure) at r.t. using PtO2 as catalyst. After filtration and evaporation the residue was partitioned between a saturated potassium-carbonate solution and ether. The ether layer was dried (K2CO3), cooled and treated with triethylamine (2.23 g. 0.022 mol) and propionylchloride (2.05 g, 0.033 mol). Stirring at r.t. for one hour followed by filtration and evaporation gave an oil which was eluated twice through an Al2O3 with ether. Evaporation of the ether gave 4.8 g of pure methyl-3-(1-propionylpiperdin-3-yl)benzoate as an oil, which could not be crystallized.

Workup

  1. customat r.t.
  2. filtrationAfter filtration and evaporation the residue
  3. customwas partitioned between a saturated potassium-carbonate solution and ether
  4. dry with materialThe ether layer was dried (K2CO3)
  5. temperaturecooled
  6. filtrationfollowed by filtration and evaporation
  7. customgave an oil which
  8. customEvaporation of the ether

Sources & evidence

ORD record
ord-e70f9b7171184b7390ed5bcd6036c9d6
Source dataset
uspto-grants-1988_01
Patent number
US04719219

Reaction notes

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