2-ethoxy-4-[N-{1-(2-piperidino-phenyl)-1-butyl)-aminocarbonylmethyl]-benzyl chloride → 2-Ethoxy-4-[N-{1-(2-piperidino-phenyl)-1-butyl}aminocarbonylmethyl]-toluene

HRID 1587076Notes

Reaction equation

HRID 1587076 reaction equation
[CH2:1]([O:3][C:4]1[CH:11]=[C:10]([CH2:12][C:13]([NH:15][CH:16]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=2[N:26]2[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]2)[CH2:17][CH2:18][CH3:19])=[O:14])[CH:9]=[CH:8][C:5]=1[CH2:6]Cl)[CH3:2].[H][H]>O1CCOCC1>[CH2:1]([O:3][C:4]1[CH:11]=[C:10]([CH2:12][C:13]([NH:15][CH:16]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=2[N:26]2[CH2:27][CH2:28][CH2:29][CH2:30][CH2:31]2)[CH2:17][CH2:18][CH3:19])=[O:14])[CH:9]=[CH:8][C:5]=1[CH3:6])[CH3:2]

Participants

4

Reactant 2

HCID 137473952-ethoxy-4-[N-{1-(2-piperidino-phenyl)-1-butyl)-aminocarbonylmethyl]-benzyl chlorideHCID 178418361HCID 178418361, compound

Product 1

HCID 212617732-Ethoxy-4-[N-{1-(2-piperidino-phenyl)-1-butyl}aminocarbonylmethyl]-toluene

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A mixture of 0.54 g (1.2 mmols) of 2-ethoxy-4-[N-{1-(2-piperidino-phenyl)-1-butyl}-aminocarbonylmethyl]-benzyl chloride (melting point 114°-115° C., prepared from 2-ethoxy-4-[N-{1-(2-piperidino-phenyl)-1-butyl}-aminocarbonylmethyl-benzyl alcohol and thionyl chloride in chloroform) and 10 ml of absolute dioxane was hydrogenated for 3 hours at 20° C. and a pressure of 5 bar hydrogen. The reaction mixture was then evaporated in vacuo, and the residue was taken up in a mixture of ethyl acetate and aqueous sodium carbonate. The organic phase was dried, filtered and evaporated in vacuo. The evaporation residue was purified by column chromatography on silica gel (chloroform/acetone=19/1).

Workup

  1. customThe reaction mixture was then evaporated in vacuo
  2. additionthe residue was taken up in a mixture of ethyl acetate and aqueous sodium carbonate
  3. customThe organic phase was dried
  4. filtrationfiltered
  5. customevaporated in vacuo
  6. customThe evaporation residue was purified by column chromatography on silica gel (chloroform/acetone=19/1)

Sources & evidence

ORD record
ord-7b4b0feff195435fba35f4b333060e98
Source dataset
uspto-grants-1993_06
Patent number
US05216167

Reaction notes

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