Sodium Carbonate → HCID 15232702, compound

HRID 2379728Notes

Reaction equation

HRID 2379728 reaction equation
[C:1]([C:9]1([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Br[CH2:22][CH2:23][CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.C(=O)([O-])[O-].[Na+].[Na+]>C(O)CCC>[C:1]([C:9]1([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH2:10][CH2:11][N:12]([CH2:22][CH2:23][CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH2:13][CH2:14]1)(=[O:8])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 12503(3-Bromopropyl)benzeneHCID 12405614HCID 12405614, compound

Product 1

HCID 15232702HCID 15232702, compound

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

3 g 4-benzoyl-4-phenylpiperidine was taken up in 200 ml n-butanol with 1.5 ml 1-bromo-3-phenylpropane and 10 g sodium carbonate, and refluxed for 4 hours. The resulting mixture was filtered and the filtrate concentrated in vacuo, taken up in ethyl acetate and washed with water. The ethyl acetate layer was dried over potassium carbonate and eluted through a short silica plug with 1:1 hexane/ethyl acetate. The eluted product was concentrated to dryness overnight, giving 3.14 g of product, melting point: 185°-186° C.

Workup

  1. temperaturerefluxed for 4 hours
  2. filtrationThe resulting mixture was filtered
  3. concentrationthe filtrate concentrated in vacuo
  4. washwashed with water
  5. dry with materialThe ethyl acetate layer was dried over potassium carbonate
  6. washeluted through a short silica plug with 1:1 hexane/ethyl acetate
  7. concentrationThe eluted product was concentrated to dryness overnight

Sources & evidence

ORD record
ord-708020dbf0da4a41ab40467b231d945a
Source dataset
uspto-grants-1994_11
Patent number
US05364867

Reaction notes

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