Reaktion #64141

ord-004d54879f88431ca2eb482dd4019232

Reaktionsgleichung

O=C(c1ccc(Br)cc1)N1CCC(O)(c2ccccc2O)CC1
1-(4-bromobenzoyl)-4-(2-hydroxyphenyl)-4-hydroxypiperidine
O=C([O-])[O-].[K+].[K+]
potassium carbonate
CCOC(=O)C(C)(C)Br
ethylα-bromoisobutyrate
O
water
CCOC(=O)C(C)(C)Oc1cccc(C2(O)CCN(C(=O)c3ccc(Br)cc3)CC2)c1
ethyl 3-{1-(4-bromobenzoyl)-4-hydroxypiperidin-4-yl}α,α-dimethylphenoxyacetate
Ausbeute 86.4%

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    SonstigeAfter completion of the reaction
  2. 2
    TemperaturThe reaction mixture was cooled
  3. 3
    Extraktionfollowed by extraction with chloroform
  4. 4
    TrocknenSubsequently, the extract was dried over anhydrous sodium sulfate
  5. 5
    workup.DISTILLATIONChloroform and the remained ethyl α-bromoisobutyrate was distilled off under reduced pressure

Vorschrift

801 mg of {1-(4-bromobenzoyl)-4-(2-hydroxyphenyl)-4-hydroxypiperidine was stirred for 9 hours at the ambient temperature of 100° C. in the presence of 1.20 g (8.68 mmol) of potassium carbonate in 4.00 g (20.5 ml) of ethylα-bromoisobutyrate. After completion of the reaction, The reaction mixture was cooled, and water was added thereto, followed by extraction with chloroform. Subsequently, the extract was dried over anhydrous sodium sulfate. Chloroform and the remained ethyl α-bromoisobutyrate was distilled off under reduced pressure to obtain 902 mg (86.4%) of ethyl 3-{1-(4-bromobenzoyl)-4-hydroxypiperidin-4-yl}α,α-dimethylphenoxyacetate.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US05411972uspto-grants-1995_05