1-Butanol → 4-(Diphenylmethylene)-1-(3-phenoxypropyl)piperidine oxalate

HRID 1709873Notes

Reaction equation

HRID 1709873 reaction equation
[C:1]1([C:7]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[C:8]2[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Br[CH2:21][CH2:22][CH2:23][O:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.[C:31](=[O:34])([O-:33])[O-].[Na+].[Na+].C([OH:41])CCC>>[C:25]([OH:24])(=[O:41])[C:31]([OH:33])=[O:34].[C:1]1([C:7]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[C:8]2[CH2:9][CH2:10][N:11]([CH2:21][CH2:22][CH2:23][O:24][C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[CH2:12][CH2:13]2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 4

HCID 2631-ButanolHCID 10340Sodium CarbonateHCID 68522Benzene, (3-bromopropoxy)-HCID 27625334-(Diphenylmethylene)piperidine

Product 1

HCID 230363354-(Diphenylmethylene)-1-(3-phenoxypropyl)piperidine oxalate

Procedure

A mixture of 3.3 g (0.013 mole) of 4-diphenylmethylenepiperidine, 3.3 g (0.015 mole) of (3-bromopropoxy)benzene and 5.3 g (0.05 mole) of anhydrous sodium carbonate in 100 ml of 1-butanol was heated at reflux for 20 hr. The mixture was concentrated under reduced pressure and the residue was partitioned between water and benzene. The benzene layer was washed with water and brine, dried over anhydrous sodium sulfate and concentrated under reduced pressure to give an oil as residue, the free base of the title compound. The free base was converted to the oxalic acid salt and the solid was recrystallized from absolute ethanol to yield 4.3 g (70%) of the title product as a white powder, m.p. 175°-178° C.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 20 hr
  3. concentrationThe mixture was concentrated under reduced pressure
  4. customthe residue was partitioned between water and benzene
  5. washThe benzene layer was washed with water and brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customto give an oil as residue

Sources & evidence

ORD record
ord-c0011bb27d054edeb121edf5f10be23e
Source dataset
uspto-grants-1990_08
Patent number
US04950674

Reaction notes

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