Reaktion #66571

ord-c697b6c9d3024fd39175c86015216b66

Reaktionsgleichung

O
Water
CC(C)c1ccc(O)c(CN2CCN(S(=O)(=O)c3ccccc3)CC2)c1
product
CC(C)c1ccc(O)c(CN2CCN(S(=O)(=O)c3ccccc3)CC2)c1
1-[[2-Hydroxy-5-(1-methylethyl)phenyl]methyl]-4-(phenylsulfonyl)-piperazine
CCOC(=O)CBr
ethyl bromoacetate
O=C([O-])[O-].[K+].[K+]
potassium carbonate
→
CCOC(=O)COc1ccc(C(C)C)cc1CN1CCN(S(=O)(=O)c2ccccc2)CC1
sub-title compound
CCOC(=O)COc1ccc(C(C)C)cc1CN1CCN(S(=O)(=O)c2ccccc2)CC1
Ethyl[4-(1-methylethyl)-2-[[4-(phenylsulfonyl)-1-piperazinyl]methyl]phenoxy]-acetate

Edukte

O
Water
CC(C)c1ccc(O)c(CN2CCN(S(=O)(=O)c3ccccc3)CC2)c1
product
CC(C)c1ccc(O)c(CN2CCN(S(=O)(=O)c3ccccc3)CC2)c1
1-[[2-Hydroxy-5-(1-methylethyl)phenyl]methyl]-4-(phenylsulfonyl)-piperazine
CCOC(=O)CBr
ethyl bromoacetate
O=C([O-])[O-].[K+].[K+]
potassium carbonate

Reagenzien

Keine

Lösungsmittel

CC(C)=O
acetone

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    Temperaturwas heated
  2. 2
    Temperaturunder reflux for 2 days
  3. 3
    Extraktionthe mixture was extracted with diethyl ether
  4. 4
    TrocknenThe organic extracts were dried (MgSO4)
  5. 5
    Sonstigeevaporated in vacuo
  6. 6
    Sonstigepurified by chromatography (silica, petrol—ether as eluent)

Vorschrift

A mixture of the product from step (d) (244 mg), ethyl bromoacetate (0.1 ml) and potassium carbonate (185 mg) in acetone was heated under reflux for 2 days. Water was added and the mixture was extracted with diethyl ether. The organic extracts were dried (MgSO4), evaporated in vacuo and purified by chromatography (silica, petrol—ether as eluent) to give the sub-title compound (113 mg).

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US08524715B2uspto-grants-2013_09