Sodium Carbonate → HCID 9927715, compound

HRID 2379729Notes

Reaction equation

HRID 2379729 reaction equation
[C:1]1([C:7]2([C:13](=[O:16])[CH2:14][CH3:15])[CH2:12][CH2:11][NH:10][CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Br[CH2:18][CH2:19][CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.C(=O)([O-])[O-].[Na+].[Na+]>C(O)CCC>[C:1]1([C:7]2([C:13](=[O:16])[CH2:14][CH3:15])[CH2:8][CH2:9][N:10]([CH2:18][CH2:19][CH2:20][C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[CH2:11][CH2:12]2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 12503(3-Bromopropyl)benzeneHCID 1979401-(4-phenylpiperidin-4-yl)propan-1-one

Product 1

HCID 9927715HCID 9927715, compound

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

6 g 4-phenyl-4-propionylpiperidine and 3.6 ml 1-bromo-3-phenylpropane was refluxed in 500 ml n-butanol with 10 g sodium carbonate for 16 hours. The reaction mixture was filtered through a silica plug and concentrated in vacuo. The residue was taken up in ethyl acetate and washed with water, then saturated brine and dried over potassium carbonate. The solution was concentrated in vacuo, 8 g of the residue was taken up in 150 ml acetonitrile and heated with 2.5 g fumaric acid. The resulting precipitate was collected by filtration, giving 3 g 4-phenyl-1-(3-phenylpropyl)-4-propionylpiperidine as the fumarate salt, melting point 136°-138° C.

Workup

  1. filtrationThe reaction mixture was filtered through a silica plug
  2. concentrationconcentrated in vacuo
  3. washwashed with water
  4. dry with materialsaturated brine and dried over potassium carbonate
  5. concentrationThe solution was concentrated in vacuo, 8 g of the residue
  6. temperatureheated with 2.5 g fumaric acid
  7. filtrationThe resulting precipitate was collected by filtration

Sources & evidence

ORD record
ord-cdc3b32fa47a43b782dae096eb6e91e5
Source dataset
uspto-grants-1994_11
Patent number
US05364867

Reaction notes

Loading…