HCID 20289414, compound → HCID 20289413, compound

HRID 1413998Notes

Reaction equation

HRID 1413998 reaction equation
[CH2:1]([N:5]1[CH2:10][CH:9]([CH2:11][O:12]CC2C=CC=CC=2)[O:8][CH:7]([CH2:20][O:21][CH2:22][C:23]([N:25]([CH2:29][CH2:30][CH3:31])[CH2:26][CH2:27][CH3:28])=[O:24])[CH2:6]1)[CH2:2][CH2:3][CH3:4]>C(O)(=O)C.C(Cl)(Cl)Cl.[Pd]>[CH2:1]([N:5]1[CH2:10][CH:9]([CH2:11][OH:12])[O:8][CH:7]([CH2:20][O:21][CH2:22][C:23]([N:25]([CH2:26][CH2:27][CH3:28])[CH2:29][CH2:30][CH3:31])=[O:24])[CH2:6]1)[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 1

HCID 20289414HCID 20289414, compound

Product 1

HCID 20289413HCID 20289413, compound

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolventHCID 6212ChloroformSolvent

Procedure

To a solution of 10.86 g of 2-[[4-butyl-6-[(phenylmethoxy)methyl]-2-morpholinyl]methoxy]-N,N-dipropylacetamide (0.025 mole) in 125 ml of glacial acetic acid is added 4.0 g of 10% Pd/C and the mixture is hydrogenated at 50 psi at 60° over a period of 28 hours (debenzylation taking up 94% of the calculated theory). The mixture is cooled to room temperature and the Pd/C removed via filtration through a pad of "celite" filter aid. The acetic acid is removed in vacuo yielding a pale yellow oil. The oil is taken up in 200 ml of chloroform and washed with 100 ml of saturated NaHCO3 solution. The CHCl3 layer is separated, dried over anhydrous Na2SO4 and then the CHCl3 is removed in vacuo yielding 8.2 g (95%) of crude product as a dark brown oil. The oil is chromatographed on 150 g of neutral Alumina III to give 0.5 g of forerun (eluted with 100 ml of chloroform) and 7.6 g (88%) of the desired product (eluted with 400 ml of chloroform and 200 ml of 2% methanolic chloroform). The 7.6 g of product is dried in vacuo to give the desired product, a dense yellow-orange oil.

Workup

  1. customthe Pd/C removed via filtration through a pad of "celite"
  2. filtrationfilter aid
  3. customThe acetic acid is removed in vacuo
  4. customyielding a pale yellow oil
  5. washwashed with 100 ml of saturated NaHCO3 solution
  6. customThe CHCl3 layer is separated
  7. dry with materialdried over anhydrous Na2SO4
  8. customthe CHCl3 is removed in vacuo
  9. customyielding 8.2 g (95%) of crude product as a dark brown oil
  10. customThe oil is chromatographed on 150 g of neutral Alumina III
  11. customto give
  12. wash0.5 g of forerun (eluted with 100 ml of chloroform) and 7.6 g (88%) of the desired product (eluted with 400 ml of chloroform and 200 ml of 2% methanolic chloroform)
  13. dry with materialThe 7.6 g of product is dried in vacuo

Sources & evidence

ORD record
ord-edc76559d3a64bd5bb2ac4744322b060
Source dataset
uspto-grants-1981_02
Patent number
US04252801

Reaction notes

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